4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

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135 reactions in Reaxys

2018-08-12 14h:43m:33s (UTC)

O

1. Query

O

S Cl

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='98-59-9') AND (IDE.INCHI='YYROPELSRYBVMQ-UHFFFAOYSA-N') NOT (RX.RXRN=607898))

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Cl O

S O

Rx-ID: 750452 View in Reaxys 1/135 Yield

Conditions & References und Mischen des durch Sulfurierung erhaltenen Gemisches von o- und p-toluolsulfonsaures Natrium mit POCl3 und Leiten Chlor darueber, Abdestillieren des POCl3 und Entfernen des p-Toluolsulfochlorid durch Ausfrierenlassen Patent; Fahlberg,Lists Erben; DE35211; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 1; p. 591 View in Reaxys With chlorosulfonic acid Klason; Wallin; Chemische Berichte; vol. 12; (1879); p. 1851 View in Reaxys Patent; Gilliard,Monnet and Cartier; DE98030; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 4; p. 1261 View in Reaxys Beckurts; Otto; Chemische Berichte; vol. 11; (1878); p. 2062 View in Reaxys With aluminium trichloride, sulfuryl dichloride Toehl; Eberhard; Chemische Berichte; vol. 26; (1893); p. 2942 View in Reaxys With sulfuric acid, sulfur trioxide, sodium chloride, Toluene-2-sulfonyl chloride Patent; Chem.Fabr.Weiler-ter Meer; DE385049; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 386 View in Reaxys With chlorosulfonic acid, Umruehren bei 5grad, Giessen des Gemisches auf Eis und Abtrennen der fluessig abgeschiedenen Chloride durch Dekantieren, und Trennung nach Kuehlung auf -20grad des auskrystallisierten p-Toluolsulfochlorids Patent; Gilliard,Monnet and Cartier; DE98030; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 4; p. 1261 View in Reaxys Patent; Gilliard,Monnet and Cartier; 12641; (1899); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 6; p. 1206 View in Reaxys Hempel; View in Reaxys With chlorosulfonic acid, T= -5 °C Vizgert, R.V.; Maksimenko, N.N.; Rubleva, L.I.; Journal of Organic Chemistry USSR (English Translation); vol. 23; nb. 11; (1987); p. 2144 - 2146; Zhurnal Organicheskoi Khimii; vol. 23; nb. 11; (1987); p. 2429 - 2431 View in Reaxys With chlorosulfonic acid Yoh, Soo-Dong; Tsuno, Yuho; Fujio, Mizue; Sawada, Masami; Yukawa, Yasuhide; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1989); p. 7 - 14 View in Reaxys With chlorosulfonic acid, T= 5 - 65 °C Humljan, Jan; Kotnik, Miha; Contreras-Martel, Carlos; Blanot, Didier; Urleb, Uros; Dessen, Andrea; Solmajer, Tom; Gobec, Stanislav; Journal of Medicinal Chemistry; vol. 51; nb. 23; (2008); p. 7486 - 7494 View in Reaxys 4-Substituted-benzenesulfonyl chlorides (3a–c) General procedure: To a solution of chlorosulfonic acid (22.8 mL, 344 mmol) cooled to 0 °C by keeping it in a freezing mixture of ice and salt, the substituted benzene (100 mmol) was introduced dropwise from the dropping funnel at such a rate that the temperature does not exceed 5 °C. When all the substituted benzene has been added (∼30 min), the reaction mixture was stirred for 4 h.

The reaction mixture was then poured over ice cold water and kept overnight in the refrigerator.

The precipitate formed was filtered and washed with water (2 * 10 mL) to afford the titled products (3a-c).

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

3a; mp 69-70 °C (as reported) [30] , 3b; mp 55-57 °C (as reported) [31] , 3c; mp 35-37 °C (as reported) [31] .

With chlorosulfonic acid, Time= 4.5h, T= 0 - 5 °C Al-Ansary, Ghada H.; Ismail, Mohamed A.H.; Abou El Ella, Dalal A.; Eid, Sameh; Abouzid, Khaled A.M.; European Journal of Medicinal Chemistry; vol. 68; (2013); p. 19 - 32 View in Reaxys With chlorosulfonic acid, Time= 6h, Reflux Zhao, Bingbing; Lei, Fei; Wang, Caolin; Zhang, Binliang; Yang, Zunhua; Li, Wei; Zhu, Wufu; Xu, Shan; Molecules; vol.

23; nb. 7; (2018); Art.No: 553 View in Reaxys

Cl O O

S

O

S

O Cl

Rx-ID: 750454 View in Reaxys 2/135 Yield

Conditions & References

80 %, 20 %

With chlorosulfonic acid, sodium chloride, T= -0.16 °C Iazykov, Mykyta; Canle, Moisés; Santaballa, J. Arturo; Rublova, Ludmila; Journal of Physical Organic Chemistry; vol. 31; nb. 2; (2018); Art.No: E3753 View in Reaxys With sulfuric acid, sodium chloride, Edukt 4: SO3 Patent; Chem. Fabr. Weiler-terMeer; DE385049; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 14; p. 386 View in Reaxys

Cl O

S O

Rx-ID: 5932804 View in Reaxys 3/135 Yield 92.8 %

Conditions & References 3 Product distribution / selectivity Patent; NIPPON CHEMICAL INDUSTRIAL COMPANY LIMITED; EP1666483; (2006); (A1) English View in Reaxys

68%

Starting Material: 4-methylphenylsulphonyl chloride Starting Material: 4-methylphenylsulphonyl chloride Yield=68percent; 1H-NMR (400 MHz, CDCl3): ∼ 1.0 (m, 4H), 1.15 (t, 3H), 1.2 (m, 4H), 1.35 (m, 2H), 1.45 (s, 20H), 1.6 (m, 6H), 2.1 (m, 1H), 2.4 (s, 3H), 2.65 (bt, 4H), 3.45 (m, 1H), 3.75 (m, 1H), 3.85~4.15 (m, 9H), 5.95 (bd, 1H), 6.5 (bt, 1H), 6.85 (bt, 1H), 7.25 (d, 2H), 7.7 (d, 2H).

Patent; Laboratoire L. Lafon; US6333338; (2001); (B1) English View in Reaxys

49%

Starting Material: 4-benzylsulphonyl chloride Starting Material: 4-benzylsulphonyl chloride

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Yield=49percent; 1H-NMR (400 MHz, CDCl3): ∼ 1.0 (m, 4H), 1.2 (m, 4H), 1.25 (m, 5H), 1.45 (s, 20H), 1.6 (m, 6H), 2.05 (m, 1H), 2.6 (bt, 4H), 3.5 (m, 2H), 3.9 (m, 2H), 4.0 (bs, 4H), 4.2 (q, 2H), 4.3 (q, 2H), 5.75 (bd, 1H), 6.4 (bt, 1H), 6.75 (bt, 1H), 7.55 (m, 5H).

Patent; Laboratoire L. Lafon; US6333338; (2001); (B1) English View in Reaxys Greene,F.D. et al.; Journal of the American Chemical Society; vol. 83; (1961); p. 3461 - 3468 View in Reaxys Bourgeois,P.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 279; (1974); p. 581 584 View in Reaxys Barton,D.H.R. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1978); p. 1090 - 1100 View in Reaxys Barton,D.H.R. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1978); p. 1682 - 1692 View in Reaxys Prinsen,A.J.; Cerfontain,H.; Recueil des Travaux Chimiques des Pays-Bas; vol. 84; (1965); p. 24 - 30 View in Reaxys Olijnsma,T. et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 89; (1970); p. 897 - 906 View in Reaxys Kukhar',V.P. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 41; (1971); p. 1459 - 1464,1465 - 1469 View in Reaxys Patent; Hoechst; DE2240883; (1972); ; vol. 80; nb. 133056 View in Reaxys Norris; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1978); p.

1378 View in Reaxys Farrar; Journal of the Chemical Society; (1965); p. 856 View in Reaxys Holland et al.; Journal of Medicinal Chemistry; vol. 6; (1963); p. 307,308 View in Reaxys Oae et al.; Tetrahedron; vol. 19; (1963); p. 827,831 View in Reaxys Barco et al.; Synthesis; (1974); p. 877 View in Reaxys Numanov et al.; Doklady Akademii Nauk Tadzhikskoi SSR; vol. 10; nb. 8; (1967); p. 29,30-32; ; vol. 68; nb. 104873g; (1968) View in Reaxys Pinchuk et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 47; (1977); p. 56,49 View in Reaxys Olah et al.; Journal of the American Chemical Society; vol. 95; (1973); p. 564,565 View in Reaxys Doyle et al.; Tetrahedron Letters; (1977); p. 2655 View in Reaxys Hope; Wiles; Journal of the Chemical Society; (1965); p. 5386,5390 View in Reaxys Ikutani; Bulletin of the Chemical Society of Japan; vol. 44; (1971); p. 271 View in Reaxys Schank; Schroeder; Phosphorus and Sulfur and the Related Elements; vol. 1; (1976); p. 307 View in Reaxys Mikolajczyk et al.; Tetrahedron Letters; (1975); p. 1325 View in Reaxys Gryzlova; Stepanov; Zhurnal Organicheskoi Khimii; vol. 7; (1971); p. 619,624 View in Reaxys Patent; Ciba Ltd.; CH333502; ; nb. 7523; (1960) View in Reaxys Patent; BASF; DE1112978; ; vol. 56; nb. 2382; (1962) View in Reaxys Patent; VEB Farbenfabrik Wolfen; DE1241442; (1964) View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Dykhanov et al.; Metody Polucheniya Khimicheskikh Reaktivov i Preparatov; vol. 26; (1974); p. 134,135,136; ; vol. 83; nb.

113836j; Chem. Zentralbl.; 1975, Abstr.No.6 ZH 292 View in Reaxys Patent; CIBA Ltd.; DE1026750; (1958); ; vol. 55; nb. 5428e; (1961) View in Reaxys Kresze; Wucherpfennig; Chemische Berichte; vol. 101; (1968); p. 365 View in Reaxys Wittmann et al.; Monatshefte fuer Chemie; vol. 100; (1969); p. 734 View in Reaxys Levcenko et al.; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 1273,1234 View in Reaxys Dauphin et al.; Bulletin de la Societe Chimique de France; (1967); p. 3395 View in Reaxys Patent; VEB Farbenfabr. Wolfen; GB1073003; (1967); ; vol. 67; nb. 108488; (1967) View in Reaxys 4-Toluenesulfonic acid-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentyl)-ester 4-Toluenesulfonic acid-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentyl)-ester 810 mg of 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-valeric acid is reduced in 20 ml of ether with 190 mg of lithium-aluminum hydride.

After aqueous sodium bicarbonate solution is added, the ether phase is separated, dried (Na2SO4), concentrated by evaporation, and the residue is distilled on a bulb tube.

700 mg of 2-hydroxy-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-pentanol, which is dissolved in 7 ml of pyridine and is mixed at 0° C. with 440 mg of 4-toluenesulfonic acid chloride, is obtained.

Patent; Schering Aktiengesellschaft; US6323199; (2001); (B1) English View in Reaxys 9.A : 20-acetylthiomethyl-4-nitropregn-4-en-3-one EXAMPLE 9A 20-acetylthiomethyl-4-nitropregn-4-en-3-one A solution of 20-hydroxymethyl-4-nitropregn-4-en-3-one (750 mg, 2.0 mmol) (prepared in Example 1) and tosyl chloride (400 mg, 2.1 mmol) was prepared in pyridine (2 ml) and stirred at 25° C. for 12 hours.

Patent; Merrell Pharmaceuticals Inc.; US5965550; (1999); (A) English View in Reaxys 2 : Reaction of 22-hydroxyvitamin D Compound (2) with p-toluenesulfonyl Chloride EXAMPLE 2 Reaction of 22-hydroxyvitamin D Compound (2) with p-toluenesulfonyl Chloride To a solution of alcohol (2) (28 mg, 0.036 mmol) in dry pyridide (100 μL) was added freshly recrystallized p-toluenesulfonyl chloride and the reaction was allowed to proceed for 64 h at 4° C. The reaction mixture was poured into ice/saturated NaHCO3 with stirring.

After 40 min of stirring the aqueous suspension was extracted with 4:1 (v/v) benzene/ether (3*10 mL).

The combined organic extracts were washed with saturated NaHCO3, water, saturated CuSO4, again water, dried (Na2 SO4) and evaporated.

The oily yellowish residue was purified by preparative HPLC (Zorbax-Silica column 6.2 mm*25 cm) using 2percent ethyl acetate in hexane as an eluent.

Pure tosylate (3) (26 mg, 78percent; collected at 20 mL) was obtained as a colorless oil: UV (hexane) ∼max 264 and 223 nm, min ∼ 238 nm; 1 H-NMR (CDCl3, 500 MHz): ∼ 0.059 and 0.067 (6H and 6H, each s, 2*SiMe2), 0.479 (3H, s, 18-H3), 0.528 (6H,q, J=8 Hz, 3*SiCH2), 0.877 (18H, s, 2*Si-t-Bu), 0.915 (9H, t, J=8 Hz, 3*SiCH2 CH3), 0.929 (3H, d, J=6.0 Hz, 21-H3), 1.103 and 1.141 (3H and 3H, each s, 26- and 27- H3), 2.43 (3H, s, Ar-Me), 2.80 (1H, br d, J=12.3 Hz, 9∼-H), 4.19 (1H, m, 3∼-H), 4.38 (1H, m, 1∼-H), 4.58 (1H, t, J=7.1 Hz, 22-H), 4.86 and 5.19 (1H and 1H, each s, 19 -H2), 5.99 (1H, d, J=11.2 Hz, 7-H), 6.22 (1H, d, J=11.2 Hz, 6-H), 7.32 (2H, d, J=8 Hz, Ar-H), 7.80 (2H, d, J=8 Hz, Ar-H); MS, m/z (rel intensity) 928 (M+, 1), 796 (2), 756 (3), 664 (3), 624 (47), 492 (27), 173 (100); exact mass calcd for C52 H92 O6 Si3 S 928.5922, found 928.5894.

Patent; Wisconsin Alumni Research Foundation; US5371249; (1994); (A) English View in Reaxys W.11.b : 11b

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

To a stirred solution of the resulting residue and p-toluenesulfonic chloride (14.8 g) in DMF (150 ml) was added pyridine (12.6 g) under ice-cooling and the mixture was stirred at room temperature for 2.5 hours followed by concentration to dryness.

Patent; Takeda Chemical Industries, Ltd.; US5389641; (1995); (A) English View in Reaxys 15 : EXAMPLE 20 STR68 29 mgs of DMAP was added to a solution of 1.31 g of diol (1) and 0.895 g of tosylchloride in 15 ml of pyddine at 0° C. (ice bath) under an atmosphere of nitrogen.

EXAMPLE 20 STR68 29 mgs of DMAP was added to a solution of 1.31 g of diol (1) and 0.895 g of tosylchloride in 15 ml of pyddine at 0° C. (ice bath) under an atmosphere of nitrogen.

The resulting solution was stirred at room temperature for 3 hours, poured into 5percent aqueous HCl solution and the organics extracted into EtOAc. The crude reaction product was purified by column chromatography (EtOAc-hexane 6:4) to give the tosylate 0.8354 g (41percent) as a white solid.

Also 0.5315 g (41percent) of starting material was recovered.

Patent; Schering Corporation; US5516784; (1996); (A) English View in Reaxys 9.A : 20-acetylthiomethyl-4-nitropregn-4-en-3-one EXAMPLE 9A 20-acetylthiomethyl-4-nitropregn-4-en-3-one A solution of 20-hydroxymethyl-4-nitropregn-4-en-3-one (750 mg, 2.0 mmol)(prepared in Example 1) and tosyl chloride (400 mg, 2.1 mmol) was prepared in pyridine (2 ml) and stirred at 25° C. for 12 hours.

Patent; Merrell Pharmaceuticals Inc.; US5750744; (1998); (A) English View in Reaxys Examples of sulphonyl halides which may be mentioned for process [C] according to the invention are: 4-phenyl-sulphonyl chloride 4-toluene-sulphonyl chloride 4-chlorophenyl-sulphonyl chloride 4-methoxyphenyl-sulphonyl chloride propyl-sulphonyl chloride butyl-sulphonyl chloride isobutyl-sulphonyl chloride Patent; Bayer Aktiengesellschaft; US5045547; (1991); (A) English View in Reaxys Sulphonyl halides which may be mentioned as examples for the process according to the invention are: 4-toluene-sulphonyl chloride 4-chlorophenyl-sulphonyl chloride 4-fluorophenyl-sulphonyl chloride 3-trifluoromethylphenyl-sulphonyl chloride pentafluorophenyl-sulphonyl chloride 2,5-dichlorophenyl-sulphonyl chloride 4-methoxyphenyl-sulphonyl chloride propyl-sulphonyl chloride butyl-sulphonyl chloride isobutyl-sulphonyl chloride 1-methylbutyl-sulphonyl chloride 3-chloropropyl-sulphonyl chloride 4-chlorobutyl-sulphonyl chloride pentyl-sulphonyl chloride.

Patent; Bayer Aktiengesellschaft; US5070096; (1991); (A) English View in Reaxys Suitable organic sulfonyl halides for use in carrying out the process of the invention include the following: ... hexylsulfonyl chloride trichloromethylsulfonyl chloride trifluoromethylsulfonyl chloride phenylsulfonyl chloride p-tolylsulfonyl chloride p-bromophenylsulfonyl chloride 2-naphthylsulfonyl chloride methylsulfonyl bromide

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

...

Patent; GAF Corporation; US3997519; (1976); (A) English View in Reaxys Examples of an acid halide of the Formula III or IV are as follows: ...

Diethylcarbamoyl chloride Methanesulfonyl chloride Ethanesulfonyl chloride Ethanesulfonyl bromide Tosyl chloride p-Chlorobenzenesulfonyl chloride 1,3-benzenedisulfonyl dichloride 4-chloro-1,3-benzenedisulfonyl dichloride Patent; Sumitomo Chemical Company, Limited; US4055565; (1977); (A) English View in Reaxys [General Preparation Process] Examples of chlorination are a method using carbon tetrachloride and triphenylphosphine, a method using thionyl chloride and phosphorus oxychloride and a method for converting into a leaving group using tosyl chloride, etc.

Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1333025; (2003); (A1) English View in Reaxys As specific examples of the compounds of the formula (IV) there may be mentioned: benzenesulfonylchloride, 3-methoxycarbonylbenzenesulfonylchloride, p-toluenesulfonylchloride, and methanesulfonylchloride.

Patent; NIHON BAYER AGROCHEM K.K.; EP588194; (1994); (A2) English View in Reaxys Examples of sulphonylation agents with general formula (IX) which can be mentioned include: ... p-chlorobenzenesulphonyl chloride; fluorobenzenesulphonyl chloride; nitrobenzenesulphonyl chloride; methoxybenzenesulphonyl chloride; tosyl chloride; methoxysulphonyl chloride; benzenesulphonic anhydride; p-toluenesulphonic anhydride.

Patent; Mioskowski, Charles; Wagner, Alain; Bensel, Nicolas; Pevere, Virginie; Desmurs, Jean-Roger; US2003/92946; (2003); (A1) English View in Reaxys More particularly, the protecting agents used are: triflic anhydride; methanesulphonyl chloride; trifluoromethanesulphonyl chloride; benzenesulphonyl chloride; p-toluenesulphonyl chloride.

Patent; Mioskowski, Charles; Wagner, Alain; Bensel, Nicolas; Pevere, Virginie; Desmurs, Jean-Roger; US2003/92946; (2003); (A1) English View in Reaxys , characterized in that the protecting agent is selected from: triflic anhydride; methanesulphonyl chloride; benzenesulphonyl chloride;

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

p-toluenesulphonyl chloride.

Patent; Mioskowski, Charles; Wagner, Alain; Bensel, Nicolas; Pevere, Virginie; Desmurs, Jean-Roger; US2003/92946; (2003); (A1) English View in Reaxys The following sulfonyl chlorides may be substituted for benzenesulfonyl chloride of Step One: ...

4-(Trifluoromethoxy)benzenesulfonyl chloride m-Toluenesulfonyl chloride p-Toluenesulfonyl chloride o-toluenesulfonyl chloride ...

Patent; Wu, Chengde; Anderson, C. Eric; Bui, Huong; Gao, Daxin; Kassir, Jamal; Li, Wen; Wang, Junmei; Biediger, Ronald; Chen, Jie; Market, Robert V.; US2005/49286; (2005); (A1) English View in Reaxys 4 : Example 4 Example 4 Synthesis of L-4-p-toluenesulfonyl-1,4-thiazin-3-carboxylic acid (Compound 4) 2.3 g (15.7mmol) L-1,4-thiazin-3-carboxylic acid hydrochlorate was dissolved in 17 ml THF, 77 ml 10wtpercent NaHCO3 aqueous solution was added, and 17 ml THF solution comprising 2.90 g (15.2 mmol) p-toluenesulfonyl chloride was added dropwise.

With sodium hydrogencarbonate Patent; Institute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A. China; LI, Song; XIAO, Junhai; LYU, Boqun; WANG, Hongqiang; ZHONG, Wu; WANG, Lili; ZHENG, Zhibing; XIE, Yunde; ZHOU, Xinbo; LI, Xingzhou; WANG, Xiaokui; (29 pag.); EP3327010; (2018); (A1) English View in Reaxys Cl

HS

O

S O

Rx-ID: 715131 View in Reaxys 4/135 Yield 99 %

Conditions & References With dihydrogen peroxide, zirconium(IV) chloride in water, acetonitrile, Time= 0.0166667h, T= 25 °C Bahrami, Kiumars; Khodaei, Mohammad Mehdi; Soheilizad, Mehdi; Synlett; nb. 17; (2009); p. 2773 - 2776 View in Reaxys

98 %

With N,N,N',N'-tetrachlorobenzene-1,3-disulphonamide, tetrabutyl-ammonium chloride, water in acetonitrile, Time= 0.333333h, T= 0 - 20 °C Veisi, Hojat; Ghorbani-Vaghei, Ramin; Mahmoodi, Jafar; Bulletin of the Korean Chemical Society; vol. 32; nb. 10; (2011); p. 3692 - 3695 View in Reaxys

98 %

With trichloroisocyanuric acid, water in acetonitrile, Time= 0.333333h, T= 0 - 20 °C Veisi, Hojat; Sedrpoushan, Alireza; Hemmati, Saba; Kordestani, Davood; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 187; nb. 6; (2012); p. 769 - 775 View in Reaxys

97 %

With thionyl chloride, dihydrogen peroxide in water, acetonitrile, Time= 0.0166667h, T= 25 °C Bahrami, Kiumars; Khodaei, Mohammad M.; Soheilizad, Mehdi; Journal of Organic Chemistry; vol. 74; nb. 24; (2009); p.

9287 - 9291 View in Reaxys

97 %

General procedure for the oxidative chlorination of thiols into sulfonyl chlorides General procedure: A mixture of thiol (1 mmol), 30percent H2O2 (3 mmol, 0.3 mL), and TiCl4 (1 mmol, 0.11 mL) was stirred in CH3CN at 25 °C for the time indicated in refPreviewPlaceHolderTable 1. A white solid, (TiO2) immediately precipitated. After

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

completion of the reaction as indicated by TLC, the mixture was quenched by adding H2O (10 mL), extracted with EtOAc (4 .x.

5 mL), and the extract was dried over anhydrous MgSO4. The filtrate was evaporated under vacuum to afford the analytically pure product or chromatographed by passing through a short column of silica gel, and the products were identified by comparison of their 1H and 13C NMR spectra, and melting point with authentic samples prepared by known methods.

With dihydrogen peroxide, titanium tetrachloride in water, acetonitrile, Time= 0.0166667h, T= 25 °C , chemoselective reaction Bahrami, Kiumars; Khodaei, Mohammad M.; Khaledian, Donya; Tetrahedron Letters; vol. 53; nb. 3; (2012); p. 354 - 358 View in Reaxys 96 %

With Oxone, potassium chloride in water, Time= 0.2h, T= 20 °C Madabhushi, Sridhar; Jillella, Raveendra; Sriramoju, Vinodkumar; Singh, Rajpal; Green Chemistry; vol. 16; nb. 6; (2014); p. 3125 - 3131 View in Reaxys

95 %

With dihydrogen peroxide, trichlorophosphate in water, Time= 0.5h, T= 25 °C , Micellar solution, chemoselective reaction Bahrami, Kiumars; Khodaei, Mohammad M.; Abbasi, Jamshid; Synthesis; vol. 2012; nb. 2; (2012); p. 316 - 322 View in Reaxys

93 %

With sulfuryl dichloride, potassium nitrate in acetonitrile, Time= 1h, T= 0 °C Park, Young Jun; Shin, Hyun Ho; Kim, Yong Hae; Chemistry Letters; nb. 8; (1992); p. 1483 - 1486 View in Reaxys

88 %

With 1,3-dichloro-5,5-dimethylhydantoin, acetic acid in dichloromethane, water, T= 0 - 20 °C , Inert atmosphere Pu, Yu-Ming; Christesen, Alan; Ku, Yi-Yin; Tetrahedron Letters; vol. 51; nb. 2; (2010); p. 418 - 421 View in Reaxys

86 %

Representative procedure for the synthesis of sulfonyl chlorides from the reaction of NaOCl•5H2O with thiols: To a solution of p-methylbenzenethiol (248.4 mg, 2.0mmol) in acetic acid (11 mL), NaOCl•5H2O (1.32 g, 12.0mmol) was added and stirred at room temperature for 1min. Saturated aqueous sodium thiosulfate (4 mL) and dichloromethane (20 mL) was added to the reaction mixture. The organic layer was separated and the aqueous phase was extracted with dichloromethane (20 mL).

The extracts were dried over anhydrous sodium sulfate, and evaporated to afford p-toluenesulfonyl chloride (328.9 mg, 86percent) as colorless crystals. This product is pure enough without further purifications, and is consistent with the commercial reagent.

With sodium hypochlorite pentahydrate, acetic acid, Time= 0.0166667h, T= 20 °C Okada, Tomohide; Matsumuro, Hiroaki; Iwai, Toshiaki; Kitagawa, Saori; Yamazaki, Kento; Akiyama, Tomomi; Asawa, Tomotake; Sugiyama, Yukihiro; Kimura, Yoshikazu; Kirihara, Masayuki; Chemistry Letters; vol. 44; nb. 2; (2015); p. 185 187 View in Reaxys

85 %

With chloro-trimethyl-silane, potassium nitrate in dichloromethane, Time= 2h, T= 50 °C Prakash, G. K. Surya; Mathew, Thomas; Panja, Chiradeep; Olah, George A.; Journal of Organic Chemistry; vol. 72; nb.

15; (2007); p. 5847 - 5850 View in Reaxys

84 %

With ammonium nitrate, hydrogenchloride, oxygen in water, acetonitrile, Time= 1h, T= 60 °C , Green chemistry Jereb, Marjan; Hribernik, Luka; Green Chemistry; vol. 19; nb. 9; (2017); p. 2286 - 2295 View in Reaxys

70 %

General procedure for the preparation of sulfonyl halides from thiols General procedure: To a stirred solution of the corresponding thiol 1 (1 eq) [1]a and isopropanol (CAS: 67-63-0) (2 eq) in dichloromethane [2] (0.15 M), N-bromosuccinimide (CAS: 128-08-5) or N-chlorosuccinimide (CAS: 128-09-6) (4 or 3.5 equiv) was added portion wise1b at rt (in the case of NBS) or 0 °C (in the case of NCS). The reaction mixture is stirred at rt until starting material was not visible by TLC (approx. 1 h). Then, the mixture was diluted with cold, saturated NaHCO3, and extracted with EtOAc (x4).1c The combined organic extracts were dried over anh. Na2SO4 and concentrated in vacuo to afford the crude material. Filtration on a SiO2 column or radial chromatography using mixtures of hexanes/ethyl acetate/acetone as eluents, yielded the pure sulfonyl halides 2 or 3.

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With N-chloro-succinimide, isopropyl alcohol in dichloromethane, Time= 1h, T= 0 - 20 °C Silva-Cuevas, Carolina; Perez-Arrieta, Carlos; Polindara-García, Luis A.; Lujan-Montelongo, J. Armando; Tetrahedron Letters; vol. 58; nb. 23; (2017); p. 2244 - 2247 View in Reaxys 45 %

With chlorine dioxide in dichloromethane, Time= 3h, T= 20 °C Lezina; Rubtsova; Kuchin; Russian Journal of Organic Chemistry; vol. 47; nb. 8; (2011); p. 1249 - 1251 View in Reaxys With hydrogenchloride, alkali hypochlorite, benzene Patent; Chem. Fabr. v. Heyden; DE550685; (1928); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 531 View in Reaxys With hydrogenchloride, Chlorieren in einer Suspension Pollak; Riess; Monatshefte fuer Chemie; vol. 53/54; (1929); p. 98 View in Reaxys With tetrachloromethane, water, chlorine Patent; Chem. Fabr. v. Heyden; DE550685; (1928); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 531 View in Reaxys With chlorine, acetic acid Zincke; Frohneberg; Chemische Berichte; vol. 43; (1910); p. 840 View in Reaxys With N-chloro-succinimide, tetrabutyl-ammonium chloride, water in acetonitrile, T= 0 °C Veisi, Hojat; Ghorbani-Vaghei, Ramin; Hemmati, Saba; Mahmoodi, Jafar; Synlett; nb. 16; (2011); p. 2315 - 2320; Art.No: B11411ST View in Reaxys With 1,3-dichloro-5,5-dimethylhydantoin, water, benzyltrimethylammonium chloride in acetonitrile, Time= 0.5h, T= 0 °C Veisi, Hojat; Bulletin of the Korean Chemical Society; vol. 33; nb. 2; (2012); p. 383 - 386 View in Reaxys 4.2. General procedure for the synthesis of sulfonamides General procedure: A mixture of thiol (1 mmol), H2O2 (30percent, 3 mmol, 0.3 mL), and POCl3 (1 mmol, 0.153 g) was stirred in CH3CN (5 mL) at 25 °C for the appropriate period of time. After consumption of the thiol as indicated by TLC, a solution of amine (1 mmol) and Amberlite IRA-400 (OH-) (0.1 g, containing 0.1 mmol of OH-) in CH3CN (2 mL) was added. The resulting mixture was stirred at room temperature until TLC showed complete disappearance of substrates. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (3.x.10 mL). The combined ethyl acetate extracts were dried with MgSO4 and concentrated under reduced pressure to give the corresponding sulfonamide product in excellent yield.

With dihydrogen peroxide, trichlorophosphate in water, acetonitrile, T= 25 °C Bahrami, Kiumars; Khodaei, Mohammad M.; Abbasi, Jamshid; Tetrahedron; vol. 68; nb. 25; (2012); p. 5095 - 5101 View in Reaxys With tetrabutyl-ammonium chloride, water, chloroamine-T in acetonitrile, Time= 0.5h, T= 0 °C Veisi, Hojat; Ataee, Meral; Fatolahi, Leila; Lotfi, Shahram; Letters in Organic Chemistry; vol. 10; nb. 2; (2013); p. 111 - 117 View in Reaxys 4.2. General procedures for the conversion of thiols to sulfonic esters General procedure: To a stirred mixture of thiol (1 mmol), t-Bu4NCl (3 equiv.), and water (2.5 mmol) in CH3CN(5 ml) at 0°C, TCCA (0.75 equiv.) was added in portions as a solid for over 1–2 min. After 30 min,a solution of phenol (1.1 mmol) in triethylamine (1.1 mmol) was added to the reaction mixture for over 1–2 min. The resulting mixture was stirred at rt for 90 min until TLC showed complete disappearance of starting material (Table 2). The reaction mixture was then diluted with water(10 ml) and

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

extracted with EtOAc (3 × 10 ml). The combined ethyl acetate extracts were dried with MgSO4 and concentrated under reduced pressure to give the corresponding sulfonic ester asthe only product.

With trichloroisocyanuric acid, tetrabutyl-ammonium chloride, water in acetonitrile, Time= 0.5h, T= 0 °C Hemmati, Saba; Mojtahedi, Mohammad Majid; Abaee, Mohammad Saeed; Vafajoo, Zahra; Saremi, Shokufe Ghahri; Noroozi, Mohammad; Sedrpoushan, Alireza; Ataee, Meral; Journal of Sulfur Chemistry; vol. 34; nb. 4; (2013); p. 347 - 357 View in Reaxys With N-chloro-4-methylbenzenesulfonamide, tetrabutyl-ammonium chloride, water in acetonitrile, Time= 0.5h, T= 0 °C Maleki, Behrooz; Hemmati, Saba; Tayebee, Reza; Salemi, Sirous; Farokhzad, Yasaman; Baghayeri, Mehdi; Zonoz, Farrokhzad Mohammadi; Akbarzadeh, Elahe; Moradi, Rohollah; Entezari, Azam; Abdi, Mohammad Reza; Ashrafi, Samaneh Sedigh; Taimazi, Fereshteh; Hashemi, Majid; Helvetica Chimica Acta; vol. 96; nb. 11; (2013); p. 2147 - 2151 View in Reaxys Reaction Steps: 2 1.1: hydrogen bromide; ammonium nitrate; oxygen / acetonitrile; water / 60 °C 1.2: 6 h / 40 °C 2.1: hydrogenchloride; ammonium nitrate; oxygen / acetonitrile; water / 2 h / 60 °C / Green chemistry With ammonium nitrate, hydrogenchloride, hydrogen bromide, oxygen in water, acetonitrile Jereb, Marjan; Hribernik, Luka; Green Chemistry; vol. 19; nb. 9; (2017); p. 2286 - 2295 View in Reaxys Reaction Steps: 2 1: hydrogenchloride; ammonium nitrate; oxygen / acetonitrile; water / 1 h / 60 °C 2: hydrogenchloride; ammonium nitrate; oxygen / acetonitrile; water / 2 h / 60 °C / Green chemistry With ammonium nitrate, hydrogenchloride, oxygen in water, acetonitrile Jereb, Marjan; Hribernik, Luka; Green Chemistry; vol. 19; nb. 9; (2017); p. 2286 - 2295 View in Reaxys Reaction Steps: 2 1: hydrogen bromide; ammonium nitrate; oxygen / acetonitrile; water / 1.25 h / 60 °C 2: hydrogenchloride; ammonium nitrate; oxygen / acetonitrile; water / 2 h / 60 °C / Green chemistry With ammonium nitrate, hydrogenchloride, hydrogen bromide, oxygen in water, acetonitrile Jereb, Marjan; Hribernik, Luka; Green Chemistry; vol. 19; nb. 9; (2017); p. 2286 - 2295 View in Reaxys Reaction Steps: 2 1: hydrogen bromide; ammonium nitrate; oxygen / water; acetic acid / 1.25 h / 60 °C 2: hydrogenchloride; ammonium nitrate; oxygen / acetonitrile; water / 2 h / 60 °C / Green chemistry With ammonium nitrate, hydrogenchloride, hydrogen bromide, oxygen in water, acetic acid, acetonitrile Jereb, Marjan; Hribernik, Luka; Green Chemistry; vol. 19; nb. 9; (2017); p. 2286 - 2295 View in Reaxys

Cl

S S

O

S O

Rx-ID: 11117902 View in Reaxys 5/135 Yield 98 %

Conditions & References With dihydrogen peroxide, zirconium(IV) chloride in water, acetonitrile, Time= 0.0166667h, T= 25 °C Bahrami, Kiumars; Khodaei, Mohammad Mehdi; Soheilizad, Mehdi; Synlett; nb. 17; (2009); p. 2773 - 2776 View in Reaxys

96 %

With Oxone, potassium chloride in water, Time= 0.166667h, T= 20 °C Madabhushi, Sridhar; Jillella, Raveendra; Sriramoju, Vinodkumar; Singh, Rajpal; Green Chemistry; vol. 16; nb. 6; (2014); p. 3125 - 3131

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

View in Reaxys 95 %

With N,N,N',N'-tetrachlorobenzene-1,3-disulphonamide, tetrabutyl-ammonium chloride, water in acetonitrile, Time= 0.333333h, T= 0 - 20 °C Veisi, Hojat; Ghorbani-Vaghei, Ramin; Mahmoodi, Jafar; Bulletin of the Korean Chemical Society; vol. 32; nb. 10; (2011); p. 3692 - 3695 View in Reaxys

95 %

With trichloroisocyanuric acid, tetrabutylammomium bromide, water in acetonitrile, Time= 0.333333h, T= 0 - 20 °C Veisi, Hojat; Sedrpoushan, Alireza; Hemmati, Saba; Kordestani, Davood; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 187; nb. 6; (2012); p. 769 - 775 View in Reaxys

94 %

With dihydrogen peroxide, trichlorophosphate in water, Time= 0.5h, T= 25 °C , Micellar solution Bahrami, Kiumars; Khodaei, Mohammad M.; Abbasi, Jamshid; Synthesis; vol. 2012; nb. 2; (2012); p. 316 - 322 View in Reaxys

88 %

With chloro-trimethyl-silane, potassium nitrate in dichloromethane, Time= 4h, T= 50 °C Prakash, G. K. Surya; Mathew, Thomas; Panja, Chiradeep; Olah, George A.; Journal of Organic Chemistry; vol. 72; nb.

15; (2007); p. 5847 - 5850 View in Reaxys

83%

Representative experimental procedure to prepare sulfonylchloride from disulfides General procedure: To a stirred solution of p-tolyl disulfide ( 1b) (246.3mg, 1.0mmol) in acetonitrile (2.0mL) and water (0.2mL), N-chlorosuccinimide (802mg, 6.0mmol) was added, and the resulting mixture was stirred at room temperature for 3h.

Water (10mL) was added and the resulting mixture was extracted with ethyl acetate (20mL×3). The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. Chromatography on silica gel using n-hexane/ethyl acetate as the eluent gave the sulfonyl chloride ( 4b) (304.7mg, 83percent) as colorless crystals.

With N-chloro-succinimide in water, acetonitrile, Time= 2.3h, T= 20 °C Kirihara, Masayuki; Naito, Sayuri; Nishimura, Yuki; Ishizuka, Yuki; Iwai, Toshiaki; Takeuchi, Haruka; Ogata, Tomomi; Hanai, Honoka; Kinoshita, Yukari; Kishida, Mari; Yamazaki, Kento; Noguchi, Takuya; Yamashoji, Shiro; Tetrahedron; vol. 70; nb. 14; (2014); p. 2464 - 2471 View in Reaxys

80 %

Representative procedure for the synthesis of sulfonyl chlorides from the reaction of NaOCl•5H2O with disulfides: To a solution of di-p-tolyldisulfide (739.2 mg, 3.0mmol) in acetic acid (11 mL), NaOCl•5H2O (2.47 g, 15.0mmol) was added and stirred at room temperature for 65min. Saturated aqueous sodium thiosulfate (4 mL) and dichloromethane (15 mL) was added to the reaction mixture. The organic layer was separated and the aqueous phase was extracted with dichloromethane (15mL x 2). The combined extracts were dried over anhydrous sodium sulfate, and evaporated to afford p-toluenesulfonyl chloride (915.0 mg, 80percent) as colorless crystals. This product is pure enough without further purifications, and is consistent with the commercial reagent. mp 70-71°C (lit18 69-71°C); 1H NMR (CDCl3): 2.49 (3H, s), 7.41 (2H, d, J = 8.3 Hz), 7.93 (2H, d, J = 8.3 Hz); 13C

NMR (CDCl3): 21.83, 127.06, 130.23, 141.71, 146.79.

With sodium hypochlorite pentahydrate, acetic acid, Time= 1.08333h, T= 20 °C , Solvent Okada, Tomohide; Matsumuro, Hiroaki; Iwai, Toshiaki; Kitagawa, Saori; Yamazaki, Kento; Akiyama, Tomomi; Asawa, Tomotake; Sugiyama, Yukihiro; Kimura, Yoshikazu; Kirihara, Masayuki; Chemistry Letters; vol. 44; nb. 2; (2015); p. 185 187 View in Reaxys 61 %

With ammonium nitrate, hydrogenchloride, oxygen in water, acetonitrile, Time= 2h, T= 60 °C , Green chemistry Jereb, Marjan; Hribernik, Luka; Green Chemistry; vol. 19; nb. 9; (2017); p. 2286 - 2295 View in Reaxys With 1,3-dichloro-5,5-dimethylhydantoin, water, benzyltrimethylammonium chloride in acetonitrile, Time= 0.5h, T= 0 °C Veisi, Hojat; Bulletin of the Korean Chemical Society; vol. 33; nb. 2; (2012); p. 383 - 386 View in Reaxys

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4.3. General procedures for the conversion of disulfides to sulfonic esters General procedure: To a stirred mixture of thiol (1 mmol), t-Bu4NCl (3 equiv.), and water (2.5 mmol) in CH3CN(10 ml) at 0°C, TCCA (0.4 equiv.) was added in portions as a solid for over 1–2 min. After 30 min,a solution of phenol (1.1 mmol) in triethylamine (1.1 mmol) was added to the reaction mixture for over 1–2 min. The resulting mixture was stirred at rt for 60 min until TLC showed complete disappearance of starting material (Table 2). The reaction mixture was then diluted with water(10 ml) and extracted with EtOAc (3 × 10 ml). The combined ethyl acetate extracts were driedwith MgSO4 and concentrated under reduced pressure to give the corresponding sulfonic ester as the only product.

With trichloroisocyanuric acid, tetrabutyl-ammonium chloride, water in acetonitrile, Time= 0.5h, T= 0 °C Hemmati, Saba; Mojtahedi, Mohammad Majid; Abaee, Mohammad Saeed; Vafajoo, Zahra; Saremi, Shokufe Ghahri; Noroozi, Mohammad; Sedrpoushan, Alireza; Ataee, Meral; Journal of Sulfur Chemistry; vol. 34; nb. 4; (2013); p. 347 - 357 View in Reaxys -1

Cl

F (v4)

B FF

F

S

O N+ N

O

Rx-ID: 44378325 View in Reaxys 6/135 Yield

Conditions & References

66 %

With thionyl chloride, tris(bipyridine)ruthenium(II) dichloride hexahydrate in water, acetonitrile, Time= 20h, T= 20 °C , Sealed tube, Irradiation Májek, Michal; Neumeier, Michael; Jacobi von Wangelin, Axel; ChemSusChem; vol. 10; nb. 1; (2017); p. 151 - 155 View in Reaxys O

–O

Cl

K+

S

O

S O

O

Rx-ID: 45738798 View in Reaxys 7/135 Yield

Conditions & References 2.2 :Step (1) recovery of 9.2 g (0.041 mol) of potassium p-toluenesulfonate was added to 100 ml of petroleum ether, 4.8 g (0.041 mol) of chlorosulfonic acid was slowly added dropwise at 0-10 ° C,After the dropwise addition, the temperature was raised to 40 ° C for 3.5 h, and potassium hydrogen sulfate was filtered to obtain p-toluenesulfonyl chloride. To the new p-toluenesulfonyl chloride was added 4.1 g (0.041 mol) of potassium bicarbonate,4.8 g (0.041 mol) of ethyl L-lactate was slowly added dropwise,After the completion of the dropwise addition, the temperature was raised to 45 ° C for 5 h, and the by-product potassium chloride was recovered by filtration. The filtrate was washed with water and neutralized to remove the solvent. The yield of ethyl L-Lactate p-toluenesulfonate was 94.6percent and the purity was 96.1percent.

With chlorosulfonic acid in Petroleum ether, Time= 3.5h, T= 0 - 40 °C , Temperature, Reagent/catalyst, Solvent Patent; Qingdao Agricultural University; HAO, SHUANGHONG; CHEN, MENGQI; LI, LIXIA; (5 pag.); CN106518733; (2017); (A) Chinese View in Reaxys

HS

O

O

Cl

S S

S S

O

S O

Rx-ID: 45807269 View in Reaxys 8/135 Yield 10 %Spectr., 26

Conditions & References With ammonium nitrate, hydrogenchloride, oxygen in water, acetonitrile, Time= 1h, T= 60 °C Jereb, Marjan; Hribernik, Luka; Green Chemistry; vol. 19; nb. 9; (2017); p. 2286 - 2295

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

%Spectr., View in Reaxys 64 %Spectr.

O

O

Cl

S S

HS

O

S O

Rx-ID: 45807270 View in Reaxys 9/135 Yield

Conditions & References

11 With ammonium nitrate, hydrogenchloride, oxygen in water, acetonitrile, Time= 1h, T= 60 °C %Spectr., 89 %Spectr. Jereb, Marjan; Hribernik, Luka; Green Chemistry; vol. 19; nb. 9; (2017); p. 2286 - 2295 View in Reaxys O O

S

Cl O

HO

S O

Rx-ID: 625040 View in Reaxys 10/135 Yield 96 %

Conditions & References With 1,3,5-trichloro-2,4,6-triazine, triethylamine in acetone, Time= 20h, Heating Blotny, Grzegorz; Tetrahedron Letters; vol. 44; nb. 7; (2003); p. 1499 - 1501 View in Reaxys

96 %

1 :Place a thermometer in a 100 mL three-necked flask and add 20 mL of dichloromethane and the mixture was stirred. Using an ice-bath, the internal temperature was adjusted to 0 to 5 ° C And cooled.To this was added 380.44 mg (2.0 mmole) of paratoluenesulfonic acid monohydrate,(Trichloromethyl) carbonate(0.80 mmole, 0.40 molar) and 1.38 g (6 mmole, 3 molar) of tribasic potassium monohydrate, And the mixture was stirred for 5 minutes.To this was added 2 drops of triethylamine (about 20 mg, 0.10 times)It can be observed that bubbles are generated in the reactor when it is added. The ice-bath was then removed and the temperature was raised to room temperatureWhen stirring is continued for 30 minutes, it can be confirmed that the reaction is completed by TLC.After confirming the completion of the reaction, the reaction mixture was filtered and washed with 5 mL of dichloromethane to remove unreacted salts. The resulting solution was distilled under reduced pressure to obtain 366 mg of para-toluenesulfonyl chloride (yield: 96percent).

Stage 1: With potassium phosphate, bis(trichloromethyl) carbonate in dichloromethane, Time= 0.0833333h, T= 0 - 5 °C Stage 2: With triethylamine in dichloromethane, Time= 0.5h, T= 20 °C Patent; Hankyong National Academic Foundation; Han, Gi Chong; Kim, Mi Soo; (6 pag.); KR101522464; (2015); (B1) Korean View in Reaxys

94 %

With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine, potassium chloride, Time= 0.0333333h, T= 25 °C , Neat (no solvent) Bahrami, Kiumars; Synlett; nb. 18; (2011); p. 2671 - 2674 View in Reaxys

88.19 %

5 :0.10 mol (19.02 g) of p-toluenesulfonic acid and 0.76 g of [Bmim] Et0S03 were dissolved in 47.55 g of chloroform,Stirring, 25 ° C conditions drop 0.3 mol (34.95 g) of chlorosulfonic acid. After the addition was complete, 0.25 mol (4.5 g) of distilled water was added to the reaction mixture to remove the excess chlorosulfonic acid. The organic phase is washed with distilled water (10g), and the residual p-toluenesulfonic acid in the organic phase is extracted, and the waste water and the product layer are obtained by separating the waste water and the organic phase. The p-toluenesulfonic acid partition coefficient is the ratio of the concentration of p-toluenesulfonic acid in the product layer to the concentration in the spent acid. The partition coefficient of p-toluenesulfonic acid was 0.0497 by liquid chromatography; chloroform was recovered by distillation of the organic phase to obtain 16.80 g of p-toluenesulfonyl chloride in a yield of 88.19percent.

With chlorosulfonic acid in chloroform, Time= 2.5h, T= 25 °C , Concentration, Reagent/catalyst Patent; Jiaxing University; Zhejiang Jiahua Chemical Corporation Energy; Tu, xiaohua; Lii, dan; Wang, Hongliang; Xu, cong; Wu, jianyi; Xu, Wenmei; Zhou, dapeng; Mou, Chengping; (6 pag.); CN105503671; (2016); (A) Chinese

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

View in Reaxys With chlorine, sulfur Patent; Chem. Fabr. v. Heyden; DE499052; (1928); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 525 View in Reaxys With tetrachloromethane, chlorine, sulfur Patent; Chem. Fabr. v. Heyden; DE499052; (1928); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 525 View in Reaxys With thionyl chloride, N,N-dimethyl-formamide Patent; Du Pont de Nemours and Co.; US2888486; (1953) View in Reaxys With phosphorus pentoxide, potassium chloride, tetraethylammonium chloride, 1.) CH3CN, 60 to 65 deg C, 1.5 h, 2.) CH3CN, RT, 3 h, Yield given. Multistep reaction Oae; Togo; Bulletin of the Chemical Society of Japan; vol. 56; nb. 12; (1983); p. 3813 - 3817 View in Reaxys With chlorine-triphenylphosphine in acetonitrile, Time= 12h, Ambient temperature Kataoka, Tadashi; Iwama, Tetsuo; Setta, Tomofumi; Takagi, Atsuko; Synthesis; nb. 4; (1998); p. 423 - 426 View in Reaxys With trichloroacetonitrile, triphenylphosphine in dichloromethane, Time= 3h, Heating Chantarasriwong, Oraphin; Jang, Doo Ok; Chavasiri, Warinthorn; Tetrahedron Letters; vol. 47; nb. 42; (2006); p. 7489 7492 View in Reaxys With triethylamine in acetone, Time= 0.333333h, T= 80 °C , microwave irradiation De Luca, Lidia; Giacomelli, Giampaolo; Journal of Organic Chemistry; vol. 73; nb. 10; (2008); p. 3967 - 3969 View in Reaxys With thionyl chloride Yadav, Snehlata; Kumar, Pradeep; De Clercq, Erik; Balzarini, Jan; Pannecouque, Christophe; Dewan, Sharwan Kumar; Narasimhan, Balasubramanian; European Journal of Medicinal Chemistry; vol. 45; nb. 12; (2010); p. 5985 - 5997 View in Reaxys With trichloroacetonitrile, triphenylphosphine in acetonitrile, T= 20 °C , Inert atmosphere Kim, Joong-Gon; Jang, Doo Ok; Synlett; nb. 20; (2010); p. 3049 - 3052; Art.No: U08710ST View in Reaxys With oxalyl dichloride, N,N-dimethyl-formamide in dichloromethane, T= 0 - 20 °C Pal, Sutanuka; Pal, Sudhir Chandra; Acta Chimica Slovenica; vol. 58; nb. 3; (2011); p. 596 - 599 View in Reaxys O O

Cl

S N

Na +

HS

–

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

O

O S

Cl Cl

N S

O

O

S O

Rx-ID: 42299185 View in Reaxys 11/135 Yield

Conditions & References

64 %, 20 %

With N-chloro-succinimide in water, acetonitrile, Time= 0.25h, T= 35 °C Yang, Zhanhui; Xu, Wei; Wu, Qiuyue; Xu, Jiaxi; Journal of Organic Chemistry; vol. 81; nb. 7; (2016); p. 3051 - 3057 View in Reaxys

O –O

Cl

Na +

S

S

O

O

O

Rx-ID: 536295 View in Reaxys 12/135 Yield 94 %

Conditions & References With 1,3,5-trichloro-2,4,6-triazine, 18-crown-6 ether in acetone, Time= 20h, Heating Blotny, Grzegorz; Tetrahedron Letters; vol. 44; nb. 7; (2003); p. 1499 - 1501 View in Reaxys

93 %

5 :Place a thermometer in a 100 mL three-necked flask, add 20 mL of dichloromethane, stir with ice-bath and cool the internal temperature to 0 to 5 ° C. To this was added 388.4 mg (2.0 mmole) sodium para-toluenesulfonate, 213 mg (0.72 mmole, 0.36 molar) of bis (trichloromethyl) carbonate and 1.38 g (6 mmole, 3 molar) of potassium tertiary phosphate monohydrate Stir for 5 minutes.When two drops of triethylamine (about 20 mg, 0.10 mole ratio) were added thereto, it was also observed that bubbles were generated in the reactor as in Example 1. [The ice-bath was then removed and the temperature was raised to room temperature 30 minutes moreAfter confirming the completion of the reaction, the reaction mixture was filtered and washed with dichloromethane (10 mL) to remove unreacted salts, and the resulting solution was distilled under reduced pressure to obtain the desired compound, para-toluenesulfonyl chloride 355 Mg (yield: 93percent).

Stage 1: With potassium phosphate, bis(trichloromethyl) carbonate in dichloromethane, Time= 0.0833333h, T= 0 - 5 °C Stage 2: With triethylamine in dichloromethane, Time= 0.5h, T= 20 °C Patent; Hankyong National Academic Foundation; Han, Gi Chong; Kim, Mi Soo; (6 pag.); KR101522464; (2015); (B1) Korean View in Reaxys

87 %

With trichlorophosphate in sulfolane, acetonitrile, Time= 0.666667h, T= 68 - 72 °C Fujita, Shinsaku; Synthesis; nb. 5; (1982); p. 423 - 424 View in Reaxys With chlorosulfonic acid Rodionow; Bulletin de la Societe Chimique de France; vol. <4> 39; (1926); p. 318; Bulletin de la Societe Chimique de France; vol. <4> 45; (1929); p. 119 View in Reaxys With chlorine-triphenylphosphine in acetonitrile, Time= 15h, Ambient temperature Kataoka, Tadashi; Iwama, Tetsuo; Setta, Tomofumi; Takagi, Atsuko; Synthesis; nb. 4; (1998); p. 423 - 426 View in Reaxys Cl

O S O–

Na +

O

S O

Rx-ID: 40730651 View in Reaxys 13/135

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Yield 74 %

Conditions & References General procedure for the chlorination of isatin-3-p-toluenesulfonyl hydrazones: General procedure: Into a flame-dried round bottom flask was added the isatin-3-p-toluenesulfonylhydrazone derivative 13 (0.2 mmol, 1.0 eq.) and to this was added DCE (0.2 M, 1.0 mL).The resulting slurry was stirred at room temperature under a nonrigorous nitrogenatmosphere and to it was added pyridine (5 molpercent, 8 μL as a 10percent solution in DCE), afterwhich the reaction mixture was immersed in an 85-88 °C sand or oil bath. To this wasadded PhICl2 (2.5 eq., 0.5 mmol, 138 mg), and the reaction mixture was stirred until ahomogeneous mixture was produced and gas evolution ceased. This was deemed the endpoint for the reaction, and was subsequently confirmed by TLC analysis, which indicatedthe consumption of starting material. The reaction mixture was added directly onto acolumn and purified by gradient column chromatography using EtOAc/Hexanes as theeluent. All 3,3-dichloro-2-oxindole products were consistent with those previouslyreported in the literature.6 With pyridine, (Dichloroiodo)benzene in 1,2-dichloro-ethane, Time= 0.0166667h, T= 20 - 88 °C , Inert atmosphere, Reflux Hepples, Charlotte; Murphy, Graham K.; Tetrahedron Letters; vol. 56; nb. 35; (2015); p. 4971 - 4974; Art.No: 46455 View in Reaxys

OH

Cl

O O

S O

Rx-ID: 37358745 View in Reaxys 14/135 Yield 77 %

Conditions & References Compound 83: Compound 83: Tosyl chloride TsCl (1.01 g, 5.3 mmol) was added to the mixture of compound 81 (4.7 ml, 6 eq.) and K2CO3 (814 mg, 5.9 mmol) stirred 3 min at 80° C. and the mixture obtained was stirred 5 min more.

Then the dry mixture of K2CO3 (814 mg, 5.9 mmol), 3-hydroxybenzaldehyde (500 mg, 4.1 mmol) and NaI (73 mg) was added and the mixture obtained was stirred 16 h at 80° C. A 2M solution of NaOH (1 ml) was added and the mixture was stirred 10 min at room temperature.

After extraction with DCM-H2O-NaCl-NaOH, the organic solution was dried with Na2SO4 and concentered under vacuum.

Pure compound 83 was obtained (800 mg) with a yield of 77percent.

Molecule 83 was characterized by its 1H NMR spectrum.

With potassium carbonate Patent; ATLANTHERA; Egorov, Maxim; Goujon, Jean-Yves; Le Bot, Ronan; US2014/86843; (2014); (A1) English View in Reaxys O

O S

Cl

HO

O

B

O

HO

S O

Rx-ID: 36050344 View in Reaxys 15/135 Yield 93%

Conditions & References With phenylchlorosulfate, C43H43NO3PPdS, sodium carbonate in acetone, T= 20 - 50 °C , Inert atmosphere, Sealed tube Debergh, J. Robb; Niljianskul, Nootaree; Buchwald, Stephen L.; Journal of the American Chemical Society; vol. 135; nb.

29; (2013); p. 10638 - 10641 View in Reaxys Cl

Br

Mg

O

S O

Rx-ID: 31978860 View in Reaxys 16/135 Yield

Conditions & References Stage 1: With DABCO•(SO2)2 in tetrahydrofuran, Time= 1h, T= -40 °C , Inert atmosphere

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Stage 2: With sulfuryl dichloride in tetrahydrofuran, T= -40 - 20 °C , Inert atmosphere Woolven, Holly; Gonzalez-Rodriguez, Carlos; Marco, Isabel; Thompson, Amber L.; Willis, Michael C.; Organic Letters; vol. 13; nb. 18; (2011); p. 4876 - 4878 View in Reaxys

O

S

Cl O

S

S O

Rx-ID: 29754578 View in Reaxys 17/135 Yield

Conditions & References With water, chlorine, T= 5 - 10 °C Barbero, Margherita; Bazzi, Stefano; Cadamuro, Silvano; Dughera, Stefano; Magistris, Claudio; Venturello, Paolo; Synlett; nb. 12; (2010); p. 1803 - 1806 View in Reaxys

O

O

N O

Cl

N

O

O

S O

O

S O

Rx-ID: 30116311 View in Reaxys 18/135 Yield

Conditions & References With Iron(III) nitrate nonahydrate, lithium chloride in acetonitrile, Time= 4h, Reflux, Inert atmosphere, optical yield given as percent de Taniguchi, Tsuyoshi; Fujii, Tatsuya; Ishibashi, Hiroyuki; Journal of Organic Chemistry; vol. 75; nb. 23; (2010); p. 8126 8132 View in Reaxys Cl

H 2N

O

S O

Rx-ID: 9256894 View in Reaxys 19/135 Yield 99 %

Conditions & References Stage 1: With hydrogenchloride, acetic acid, sodium nitrite in water, acetonitrile, T= 0 - 5 °C Stage 2: With sulfur dioxide, copper dichloride in water, acetonitrile, Time= 16h, T= 20 °C Ikemoto, Norihiro; Liu, Jinchu; Brands, Karel M.J.; McNamara, James M.; Reider, Paul J.; Tetrahedron; vol. 59; nb. 8; (2003); p. 1317 - 1325 View in Reaxys Stage 1: With hydrogenchloride, sodium nitrite Stage 2: With sulfur dioxide, copper(l) chloride in acetone Pokhodylo, Nazariy T.; Matiychuk, Vasyl S.; Obushak, Mykola D.; Synthesis; nb. 14; (2009); p. 2321 - 2323; Art.No: Z03509SS View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Cl

O N S

O

S

N O

H 2N

OH

O

Rx-ID: 29124868 View in Reaxys 20/135 Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys

Cl

O S

N OH

O

S

O

H 2N

O

Rx-ID: 29124870 View in Reaxys 21/135 Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys

Cl

O S

HN O

O

OH

S O

Rx-ID: 29124872 View in Reaxys 22/135 Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys

HN

Cl

O N

S O

O

OH

S O

Rx-ID: 29124874 View in Reaxys 23/135 Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

HN Cl

O S O

O

OH

S O

Rx-ID: 29124875 View in Reaxys 24/135 Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys

Cl

O O S

S

O

N O

H 2N

OH

O

Rx-ID: 29124884 View in Reaxys 25/135 Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys O O

S

N H

Cl O

S O

HO

Rx-ID: 29124893 View in Reaxys 26/135 Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys O

NH 2 O

S

Cl O

S O

HO

Rx-ID: 29124895 View in Reaxys 27/135 Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys H N

O O

S HO

Cl O

S O

Rx-ID: 29124897 View in Reaxys 28/135

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys O

O

Cl

S

HN

S

O

O

HO

Rx-ID: 29124899 View in Reaxys 29/135 Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys O

O

Cl

S

S

O

H 2N

HO

O

Rx-ID: 29124901 View in Reaxys 30/135 Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys O O

Cl

S

NH 2

O

S O

HO

Rx-ID: 29124909 View in Reaxys 31/135 Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys O

O

Cl

S

O

N H

S O

HO

Rx-ID: 29124911 View in Reaxys 32/135 Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys O

H 2N

O

S

Cl O

HO

S O

Rx-ID: 29124913 View in Reaxys 33/135

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys H N

Cl

O O

S

O

S O

HO

Rx-ID: 29124915 View in Reaxys 34/135 Yield

Conditions & References With 1,3,5-trichloro-2,4,6-triazine in acetonitrile, Time= 0.5h, T= 20 °C Rad, Mohammad Navid Soltani; Khalafi-Nezhad, Ali; Asrari, Zeinab; Behrouz, Somayeh; Amini, Zohreh; Behrouz, Marzieh; Synthesis; nb. 23; (2009); p. 3983 - 3988; Art.No: Z15009SS View in Reaxys

O

O

O N

N

N N O N

O O

S

Cl O

S O

O

N

Rx-ID: 27906897 View in Reaxys 35/135 Yield

Conditions & References P.66 : Reference Preparation Example 66 Reference Preparation Example 66 20percent sodium ethoxide and isoamyl nitrite were added to and dissolved in an ethanol solution of 5-(cyanomethyl)-2-methoxybenzonitrile.

Isopropyl alcohol was added, and the precipitate formed was collected by filtration.

The resulting solid and 4-methylbenzenesulfonyl chloride were dissolved in ethanol, and the solution was refluxed for 5 hours to obtain 5-[cyano({[(4-methylphenyl)sulfonyl]oxy}imino)methyl]-2-methoxybenzonitrile. AP: 378.

With sodium ethanolate in ethanol Patent; Astellas Pharma Inc.; EP1992361; (2008); (A1) English View in Reaxys

O S

Al

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O

N+

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Cl –

2018-08-12 14:44:40

4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

O

O

Cl

S O

S O

Rx-ID: 28231855 View in Reaxys 36/135 Yield 47 %, 50 %

Conditions & References in dichloromethane, Time= 0.5h, T= 20 °C Signore; Malanga; Menicagli; Tetrahedron; vol. 64; nb. 49; (2008); p. 11218 - 11223 View in Reaxys Cl

O S–

Na +

S

O

O

O

Rx-ID: 23747914 View in Reaxys 37/135 Yield 93.9 %

Conditions & References 1 :<Fifth step>; A reactor was charged with 29.3 g of sodium benzenesulfinate (0.14 mole) obtained by the fourth step, and the benzenesulfinate was dissolved in 65 mL of water. Then, 105 mL of toluene was charged, and 10.3 g (0.1456 mole, 1.04 times moles) of chlorine was, little by little, blown into the reactor at a temperature of 18 to 20 °C. The reaction solution was aged at the same temperature of 18 to 20 °C with stirring, and separated into an organic layer and an aqueous layer. The organic layer was washed with 90 g of a 3percent aqueous sodium chloride solution and then concentrated at a reduced pressure and 45°C or less to obtain 32. 9 g of a benzenesulfonyl chloride solution. Gas chromatographic quantitative analysis revealed that the concentration of benzenesulfonyl chloride in the organic layer was 70.7percent (weight; 24.21g, 0.1371 mole), and the yield was 93.9percent. Identification data: EI-MS M+:176 m/z With chlorine in water, toluene, Product distribution / selectivity Patent; NIPPON CHEMICAL INDUSTRIAL COMPANY LIMITED; EP1666483; (2006); (A1) English View in Reaxys

Cl

O

O

N+

N

Cl –

S

O

N O

S O

O O N O

Rx-ID: 9639623 View in Reaxys 38/135 Yield 43 %

Conditions & References With sulfur dioxide in acetic acid, acetone, T= 15 - 20 °C Bilaya; Obushak; Buchinskii; Ganushchak; Russian Journal of Organic Chemistry; vol. 40; nb. 2; (2004); p. 191 - 194 View in Reaxys Cl

Br

O

S O

Rx-ID: 9519540 View in Reaxys 39/135 Yield

Conditions & References Stage 1: With iodine, magnesium in tetrahydrofuran, Time= 1h, Heating Stage 2: With sulfur dioxide in tetrahydrofuran, Time= 0.5h, T= -40 °C Stage 3: With sulfuryl dichloride in tetrahydrofuran, T= -40 - 20 °C

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Pandya, Rina; Murashima, Takashi; Tedeschi, Livio; Barrett, Anthony G. M.; Journal of Organic Chemistry; vol. 68; nb.

21; (2003); p. 8274 - 8276 View in Reaxys Cl

O N

O

N

S

N

NH

H 2N

N

N

H N

N

O

N O

S

N N

Cl

NH N

O

N

S

NH

O

N

N

N

N N H

N N

N

N

N

Rx-ID: 5284585 View in Reaxys 40/135 Yield

Conditions & References in dichloromethane, Time= 1461h, T= 20 °C , Condensation Berecz, Gabor; Reiter, Jozsef; Csaszar, Janos; Journal of Heterocyclic Chemistry; vol. 36; nb. 5; (1999); p. 1199 - 1212 View in Reaxys

Cl

N C+ N

Cl Cl –

O

S O

Rx-ID: 24729339 View in Reaxys 41/135 Yield 93.2%

Conditions & References 10 : Synthesis of p-toluenesulfonyl chloride Example 10 Synthesis of p-toluenesulfonyl chloride To 9.72 g (0.0575 mole) of 2-chloro-1,3-dimethylimidazolinium chloride, 83 g of toluene was added and successively 8.61 g (0.05 mole) of p-toluenesulfonic acid was added.

The mixture was reacted at 110° C. for 4 hours.

The reaction mass was analyzed by gas chromatography. p-Toluenesulfonyl chloride was obtained in the yield of 93.2percent.

With toluene-4-sulfonic acid in toluene Patent; Mitsui Toatsu Chemicals, Inc.; US5750779; (1998); (A) English View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Cl

O

O

N

N+

Cl –

S

O

N O

S O

O O N O

Rx-ID: 4870237 View in Reaxys 42/135 Yield

Conditions & References

43 %

With sulfur dioxide in acetic acid, acetone Obushak; Buchinskii; Bilaya; Ganushchak; Russian Journal of General Chemistry; vol. 67; nb. 8; (1997); p. 1317 - 1317 View in Reaxys Cl S

O

H 2N

O

Rx-ID: 24596883 View in Reaxys 43/135 Yield

Conditions & References 9 : N-t-Butylbenzenesulfonamide Preparation 9 N-t-Butylbenzenesulfonamide Using a procedure analogous to that described in Preparation 5, from 4-methylbenzenesulfonyl chloride (2.65 g) and t-butylamine (3.29 g) was obtained 3.0 g of the title compound: m.p. 77°-80° C. Patent; Pfizer Inc.; US5665749; (1997); (A) English View in Reaxys O

O

O

S

O S

N HO

O O

O O

S

S N

O

O O

Cl

S

O

O

S

S HO

O

O

Rx-ID: 4519842 View in Reaxys 44/135 Yield

Conditions & References

20 %, 70 %, With air in chloroform, Time= 12h, Ambient temperature, various reaction conditions, Product distribution, Mechanism 5% Balakirev, Maxim Yu.; Khramtsov, Valery V.; Journal of Organic Chemistry; vol. 61; nb. 21; (1996); p. 7263 - 7269 View in Reaxys Cl

4-CH3C6H4SnR3

O

S O

Rx-ID: 5932805 View in Reaxys 45/135

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Yield

Conditions & References With sulfuryl dichloride, Time= 4h, T= 20 °C Lube, Andreas; Neumann, Wilhelm P.; Niestroj, Michael; Chemische Berichte; vol. 128; nb. 12; (1995); p. 1195 - 1198 View in Reaxys Cl

O S

O

HO

S O

Rx-ID: 103054 View in Reaxys 46/135 Yield 81 %

Conditions & References With tert-butylhypochlorite in dichloromethane, Time= 2h, Ambient temperature, chloramine-T, CH2Cl2, RT Furukawa; Nishikawa; Inaba; et al.; Chemical and Pharmaceutical Bulletin; vol. 29; nb. 3; (1981); p. 623 - 628 View in Reaxys With water, chlorine Otto; v.Gruber; Justus Liebigs Annalen der Chemie; vol. 142; (1867); p. 101 View in Reaxys With N-chloro-succinimide in tetrahydrofuran, Ambient temperature, Irradiation, Yield given Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7911 - 7914 View in Reaxys Reaction Steps: 2 1: 81 percent / CH2Cl2 / 2 h / Ambient temperature 2: 1.) n-butyllithium, 2.) SO2Cl2 / 1.) THF, hexane, -78 deg C, 2.) -78 deg C, 20 min With n-butyllithium, sulfuryl dichloride in dichloromethane Crich, David; Ritchie, Timothy J.; Tetrahedron; vol. 44; nb. 8; (1988); p. 2319 - 2328 View in Reaxys

Cl

O

O

S

O

S

O N

Cl

O

O NH 2

Rx-ID: 3986019 View in Reaxys 47/135 Yield 82 %

Conditions & References With N-chloro-succinimide in tetrahydrofuran, Time= 16h, Ambient temperature, Irradiation Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7911 - 7914 View in Reaxys

Cl

O

Cl

O

S

S

Cl

Cl

N

O

O NH 2

Rx-ID: 3986787 View in Reaxys 48/135

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Yield

Conditions & References

95 %

With N-chloro-succinimide in tetrahydrofuran, Time= 16h, Ambient temperature, Irradiation Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7911 - 7914 View in Reaxys

O S N

O NH 2

Cl

Cl

O

S O

Rx-ID: 3986798 View in Reaxys 49/135 Yield

Conditions & References

88 %

With N-chloro-succinimide in tetrahydrofuran, Time= 16h, Ambient temperature, Irradiation Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7911 - 7914 View in Reaxys

88 %

With N-chloro-succinimide in tetrahydrofuran, Time= 16h, Ambient temperature, Irradiation, reactions of N-substituted-N-tosylhydrazines with NCS and NBS, Product distribution, Mechanism Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7911 - 7914 View in Reaxys

O S N

O NH 2

Cl O

S

Cl

O

Rx-ID: 3996196 View in Reaxys 50/135 Yield 68 %

Conditions & References With N-chloro-succinimide in tetrahydrofuran, Time= 16h, Ambient temperature, Irradiation Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7911 - 7914 View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Cl

O

O

S

S

Cl N

O

O NH 2

Rx-ID: 3996489 View in Reaxys 51/135 Yield 57 %

Conditions & References With N-chloro-succinimide in tetrahydrofuran, Time= 16h, Ambient temperature, Irradiation Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7911 - 7914 View in Reaxys O

O

Cl

S NH

O

S

sulfate diethylamine

O

Rx-ID: 18269254 View in Reaxys 52/135 Yield

Conditions & References Reaction Steps: 2 1: 1.) base, 2.) O-(2,4-dinitrophenyl)hydroxylamine 2: NCS / tetrahydrofuran / 16 h / Ambient temperature; Irradiation With N-chloro-succinimide, O-(2,4-dinitrophenyl)hydroxylamine in tetrahydrofuran Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7911 - 7914 View in Reaxys

O Cl

S NH

O

O

S

sulfate diethylamine

O

Rx-ID: 18269287 View in Reaxys 53/135 Yield

Conditions & References Reaction Steps: 2 1: 1.) base, 2.) O-(2,4-dinitrophenyl)hydroxylamine 2: NCS / tetrahydrofuran / 16 h / Ambient temperature; Irradiation With N-chloro-succinimide, O-(2,4-dinitrophenyl)hydroxylamine in tetrahydrofuran Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7911 - 7914 View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

O S NH

O

Cl O

S

sulfate diethylamine

O

Rx-ID: 18269303 View in Reaxys 54/135 Yield

Conditions & References Reaction Steps: 2 1: 1.) base, 2.) O-(2,4-dinitrophenyl)hydroxylamine 2: NCS / tetrahydrofuran / 16 h / Ambient temperature; Irradiation; reactions of N-substituted-N-tosylhydrazines with NCS and NBS With N-chloro-succinimide, O-(2,4-dinitrophenyl)hydroxylamine in tetrahydrofuran Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7911 - 7914 View in Reaxys

Cl

Cl

O

O

S NH

S

sulfate diethylamine

O

O

Rx-ID: 18279022 View in Reaxys 55/135 Yield

Conditions & References Reaction Steps: 2 1: 1.) base, 2.) O-(2,4-dinitrophenyl)hydroxylamine 2: NCS / tetrahydrofuran / 16 h / Ambient temperature; Irradiation With N-chloro-succinimide, O-(2,4-dinitrophenyl)hydroxylamine in tetrahydrofuran Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7911 - 7914 View in Reaxys

Cl

O

O S NH

O

S

sulfate diethylamine

O

O

Rx-ID: 18279033 View in Reaxys 56/135 Yield

Conditions & References Reaction Steps: 2 1: 1.) base, 2.) O-(2,4-dinitrophenyl)hydroxylamine 2: NCS / tetrahydrofuran / 16 h / Ambient temperature; Irradiation With N-chloro-succinimide, O-(2,4-dinitrophenyl)hydroxylamine in tetrahydrofuran

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7911 - 7914 View in Reaxys O

O

Cl

S S

S

O

Cl

S O

Rx-ID: 1700488 View in Reaxys 57/135 Yield

Conditions & References With sulfuryl dichloride, potassium nitrate, Yield given. Yields of byproduct given Park, Young Jun; Shin, Hyun Ho; Kim, Yong Hae; Chemistry Letters; nb. 8; (1992); p. 1483 - 1486 View in Reaxys

Cl

O N O

S

O

S O

HO

Rx-ID: 2326127 View in Reaxys 58/135 Yield

Conditions & References

99 %

With sulfuryl dichloride, triphenylphosphine in dichloromethane, Time= 1h, Ambient temperature Huang, Jianxing; Widlanski, Theodore S.; Tetrahedron Letters; vol. 33; nb. 19; (1992); p. 2657 - 2660 View in Reaxys

HS

o-chloro-benzoate potassium Cl

O

S

monosodium-salt of/the/ 4-hydroxy-benzene-sulfonic acid-(1)

O

Rx-ID: 19755143 View in Reaxys 59/135 Yield

Conditions & References Reaction Steps: 2 1: SO2Cl2 2: SO2Cl2, KNO3 With sulfuryl dichloride, potassium nitrate Park, Young Jun; Shin, Hyun Ho; Kim, Yong Hae; Chemistry Letters; nb. 8; (1992); p. 1483 - 1486 View in Reaxys

Cl

Cl O

O

Cl

S

O

S O

S

O

Cl

O

S O

O

Rx-ID: 3072107 View in Reaxys 60/135 Yield 65 %, 23 %

Conditions & References With chlorine in water, acetic acid, Time= 8h, T= 20 - 30 °C Baum, James Clayton; Durkin, Kathleen Anne; Precedo, Laura; O'Blenes, Stacy Brian; Goehl, John Edward; et al.; Canadian Journal of Chemistry; vol. 69; nb. 12; (1991); p. 2127 - 2135 View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Cl

Cl

O

Cl

O

Cl

O

S

O

S

S S

Cl

O

Cl

O

O

O

Rx-ID: 3073548 View in Reaxys 61/135 Yield

Conditions & References

56 %, 23 %

With chlorine in water, acetic acid, Time= 8h, T= 20 - 30 °C Baum, James Clayton; Durkin, Kathleen Anne; Precedo, Laura; O'Blenes, Stacy Brian; Goehl, John Edward; et al.; Canadian Journal of Chemistry; vol. 69; nb. 12; (1991); p. 2127 - 2135 View in Reaxys

O

O S

OH

OH

O

H

Cl

O

H

H H

S

O

O

O H

O H

O

OH

OH

S O

O

Rx-ID: 3429883 View in Reaxys 62/135 Yield

Conditions & References

39 %, 7 %, 42 %

With pyridine, Time= 2h, T= 0 °C Nakayama, Juzo; Hirashima, Atsushi; Journal of the American Chemical Society; vol. 112; nb. 21; (1990); p. 7648 - 7653 View in Reaxys

O O

O

O S

O

O S

Cl

O S O

O

O

S O

Cl

Rx-ID: 2838842 View in Reaxys 63/135 Yield

Conditions & References With n-butyllithium, sulfuryl dichloride, 1.) THF, hexane, -78 deg C, 2.) -78 deg C, 20 min, Yield given. Yields of byproduct given. Title compound not separated from byproducts Crich, David; Ritchie, Timothy J.; Tetrahedron; vol. 44; nb. 8; (1988); p. 2319 - 2328 View in Reaxys With n-butyllithium, sulfuryl dichloride, 1.) THF, hexane, -78 deg C, 2.) -78 deg C, 20 min, Yield given. Multistep reaction.

Yields of byproduct given Crich, David; Ritchie, Timothy J.; Tetrahedron; vol. 44; nb. 8; (1988); p. 2319 - 2328 View in Reaxys

O

S

O

S

S I

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

O

O

O

Cl

S

O

S

S S

O

O

S O

O

Rx-ID: 2087031 View in Reaxys 64/135 Yield

Conditions & References

1.21 g, 1.81 g, 1.52 g, 0.62 g

With 2,2'-azobis(isobutyronitrile) in tetrachloromethane, Time= 9h, Heating, Further byproducts given da Silva Correa, Carlos M.M.; Oliveira, Maria Augusta B.C.S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 811 - 814 View in Reaxys O

O

O

S

O

S

S

S

S

I

O

O

O

O

O

O

O

S

S

O S

O

Cl

S

O

S O

Rx-ID: 2087032 View in Reaxys 65/135 Yield

Conditions & References

1.52 g, 1.81 g, 1.21 g, 2.03 g, 0.62 g

With 2,2'-azobis(isobutyronitrile) in tetrachloromethane, Time= 9h, Heating, Product distribution da Silva Correa, Carlos M.M.; Oliveira, Maria Augusta B.C.S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 811 - 814 View in Reaxys O

O O

O

S

S

S

O

I

O

O

O

O

O

O

S

S

O O

S

S

Cl O

S O

Rx-ID: 2087033 View in Reaxys 66/135 Yield

Conditions & References

1.81 g, 1.52 g, 2.03 g, 0.62 g

With 2,2'-azobis(isobutyronitrile) in tetrachloromethane, Time= 9h, Heating, Further byproducts given da Silva Correa, Carlos M.M.; Oliveira, Maria Augusta B.C.S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 811 - 814 View in Reaxys O

O O

O

S

S

S I

O

O

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

O

O

O

S

O O

O

S O

Cl

S O

N

S O

Rx-ID: 2087034 View in Reaxys 67/135 Yield

Conditions & References

1.81 g, 2.03 g, 0.42 g, 0.62 g

With 2,2'-azobis(isobutyronitrile) in tetrachloromethane, Time= 9h, Heating, Further byproducts given da Silva Correa, Carlos M.M.; Oliveira, Maria Augusta B.C.S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 811 - 814 View in Reaxys

O Se

O

S

Se

NH

H 2N O

O

Cl

S Se

S

O

O

Rx-ID: 3444277 View in Reaxys 68/135 Yield

Conditions & References

83 %, 11 %

With sulfuryl dichloride, triethylamine in pyridine, dichloromethane, T= 0 °C , various reagents for preparation of diverse selenosulfonates; mechanism is proposed, Product distribution Back, Thomas G.; Collins, Scott; Krishna, M. Vijaya; Canadian Journal of Chemistry; vol. 65; (1987); p. 38 - 42 View in Reaxys

H N

Cl

NH O

O

S

S O

O

Rx-ID: 1493808 View in Reaxys 69/135 Yield

Conditions & References

13 %, 81 %

in pyridine, 1)50 deg C, 2h 2)room temp., 20h Antonova, A. Ts.; Simov, D.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 20; nb. 6; (1984); p.

618 - 621; Khimiya Geterotsiklicheskikh Soedinenii; vol. 20; nb. 6; (1984); p. 765 - 768 View in Reaxys

O

Si

S Cl

Cl Cl O

Cl

O S

Si

O S

S O

Si

Rx-ID: 1624457 View in Reaxys 70/135

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Yield

Conditions & References

66 %

With aluminium trichloride in diethyl ether, Ambient temperature Vorob'eva, I. S.; Stadnichuk, M. D.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 9; (1984); p. 2064 - 2075,1843 - 1852 View in Reaxys

O S Cl

Cl

Cl

O

Cl

S

O S

S

O

O

Rx-ID: 1624462 View in Reaxys 71/135 Yield

Conditions & References

33 %

With aluminium trichloride in diethyl ether, Ambient temperature Vorob'eva, I. S.; Stadnichuk, M. D.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 9; (1984); p. 2064 - 2075,1843 - 1852 View in Reaxys

O

Si

S Cl

Cl

O

Cl

Cl

S

S

S

O

O

Si Si

O

Rx-ID: 1624472 View in Reaxys 72/135 Yield

Conditions & References

57 %

With aluminium trichloride in diethyl ether, Ambient temperature Vorob'eva, I. S.; Stadnichuk, M. D.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 9; (1984); p. 2064 - 2075,1843 - 1852 View in Reaxys

H O

OH

H

O S O

O O

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

O

O

Cl

O

S

O

H

H O

H

O

OH

OH

O

Rx-ID: 1693649 View in Reaxys 73/135 Yield

Conditions & References

533 mg, 3.5 mg, 31 mg, 43 mg

Time= 0.25h, Heating Hanson, James R.; Yang-zhi, Ling; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1984); p. 2173 - 2176 View in Reaxys

H

O S O

O O

O

O

Cl

O

O

H

H O

H

S O

OH

OH

O

Rx-ID: 3164710 View in Reaxys 74/135 Yield

Conditions & References

533 mg, 3.5 mg, 31 mg, 43 mg

With formic acid, Time= 0.25h, Heating Hanson, James R.; Yang-zhi, Ling; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1984); p. 2173 - 2176 View in Reaxys

O

Cl N

S

O S

N

HO

Cl

O O

S O

Rx-ID: 1498944 View in Reaxys 75/135 Yield 50 %, 36 %

Conditions & References in dichloromethane, Time= 0.5h, Ambient temperature Nishikawa; Inaba; Furukawa; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 4; (1983); p. 1374 - 1377 View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

O

Cl O

Cl

S

N S

O O

N

HO

S O

O O

Rx-ID: 1501328 View in Reaxys 76/135 Yield 76 %, 10 %

Conditions & References in dichloromethane, Time= 0.5h, Ambient temperature Nishikawa; Inaba; Furukawa; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 4; (1983); p. 1374 - 1377 View in Reaxys O

O

Cl

S

O N

S HO

N

O

Cl

S O

Rx-ID: 1700537 View in Reaxys 77/135 Yield 50 %, 41 %

Conditions & References in dichloromethane, Time= 0.5h, Ambient temperature Nishikawa; Inaba; Furukawa; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 4; (1983); p. 1374 - 1377 View in Reaxys O

O S Cl

O

Cl

N

N S

S

O

HO

O

Rx-ID: 1700556 View in Reaxys 78/135 Yield 60 %, 32 %

Conditions & References in dichloromethane, Time= 0.5h, Ambient temperature Nishikawa; Inaba; Furukawa; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 4; (1983); p. 1374 - 1377 View in Reaxys

H 2N

O

O S

Cl

H 2N

O

NH S HO

O

Cl

N

S O

Rx-ID: 1700564 View in Reaxys 79/135 Yield 57 %, 36 %

Conditions & References in dichloromethane, Time= 0.5h, Ambient temperature Nishikawa; Inaba; Furukawa; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 4; (1983); p. 1374 - 1377 View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

O

O

Cl

S

O

NH

HN

S HO

S

O

Cl

O

Rx-ID: 1700571 View in Reaxys 80/135 Yield

Conditions & References

46 %, 42 %

in dichloromethane, Time= 0.5h, Ambient temperature Nishikawa; Inaba; Furukawa; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 4; (1983); p. 1374 - 1377 View in Reaxys O

O

H 2N

N

Cl

O

S

Cl

S

O

N

HO

S O

H 2N

Rx-ID: 1700586 View in Reaxys 81/135 Yield

Conditions & References

39 %, 40 %

in dichloromethane, Time= 0.5h, Ambient temperature Nishikawa; Inaba; Furukawa; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 4; (1983); p. 1374 - 1377 View in Reaxys

O

O

O

Cl

S NH

N

S

O

O

Rx-ID: 2177969 View in Reaxys 82/135 Yield

Conditions & References With phosphorus pentachloride, T= 100 °C , Product distribution L'abbe, Gerrit; Asch, Alex Van; Godts, Francoise; Bulletin des Societes Chimiques Belges; vol. 92; nb. 1; (1983); p. 79 - 80 View in Reaxys O Cl

O

O

S

Cl

N S

N

N

O

N

HO

N

S O

N

Rx-ID: 3427377 View in Reaxys 83/135 Yield 31 %, 43 %

Conditions & References in dichloromethane, Time= 0.5h, Ambient temperature Nishikawa; Inaba; Furukawa; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 4; (1983); p. 1374 - 1377 View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

O

N O

S

I

N

I

O

O

O

O

O

O

S

S

O O

O

S

S

S

Cl

Cl

O

S O

Rx-ID: 3879974 View in Reaxys 84/135 Yield

Conditions & References

82 %, 78 %, in tetrachloromethane, Time= 2h, T= 0 °C , Product distribution 1% Correa, Carlos M. M. da Silva; Oliveira, Maria Augusta B. C. S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 711 - 716 View in Reaxys

O

N O

S

Br

N

Br

O

O S

O O S

S

Cl

Cl O

S O

Rx-ID: 3879977 View in Reaxys 85/135 Yield

Conditions & References

67 %, 56 %, in tetrachloromethane, Time= 30h, Heating, Product distribution 6% Correa, Carlos M. M. da Silva; Oliveira, Maria Augusta B. C. S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 711 - 716 View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

O O S O

F

O

O F Cl

H O

O H

H

S O

H

O

Rx-ID: 25060041 View in Reaxys 86/135 Yield

Conditions & References 49 : EXAMPLE 49 EXAMPLE 49 In a manner analogous to example 15, when [1∼,3∼]-1,3-dibenzyloxy-25-(1-ethoxyethoxy)-24,24-difluorocholest-5-en-21-ol is reacted with pyridine and p-toluenesulfonyl chloride, [1∼,3∼]-1,3-dibenzyloxy-25-(1-ethoxyethoxy)-24,24-difluorocholest-5-en-21-ol 21-(4-methylbenzenesulfonate) can be obtained.

Patent; Hoffmann-La Roche Inc.; US4421690; (1983); (A) English View in Reaxys

O O S O

F

O

O F Cl

H

O

Si O

S O

H

H

H

O Si

Rx-ID: 25060042 View in Reaxys 87/135 Yield

Conditions & References 50 : EXAMPLE 50 EXAMPLE 50 In a manner analogous to example 15, when [1∼,3∼]-1,3-bis(t-butyldimethylsilyloxy)-25-(1-ethoxyethoxy)-24,24-difluorocholest-5-en-21-ol is reacted with pyridine and p-toluenesulfonyl chloride, [1∼,3∼]-1,3-bis(t-butyldimethylsilyloxy)-25-(1-ethoxyethoxy)-24,24-difluorocholest-5-en-21-ol 21-(4-methylbenzenesulfonate) can be obtained.

Patent; Hoffmann-La Roche Inc.; US4421690; (1983); (A) English View in Reaxys

O O

S

O O

Cl

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S HO

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

O

Cl

O

O O

O

S

O

S HO

S

O

S

O

HO

Cl

Rx-ID: 3537664 View in Reaxys 88/135 Yield

Conditions & References

1.8 % Chro- With chlorosulfonic acid, Time= 1.5h, T= 25 °C , Product distribution mat., 3.2 % Krylov, E. N.; Khokhlova, S. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 52; nb. 2; (1982); p. 390 - 393,341 - 343 Chromat., View in Reaxys 11.6 % Chromat., 85.2 % Chromat., 82.1 % Chromat., 16.1 % Chromat.

Cl

Cl Cl

S

O Cl

O

Rx-ID: 25122155 View in Reaxys 89/135 Yield

Conditions & References 11 : EXAMPLE 11 EXAMPLE 11 172 g (1 mol) of p-toluenesulphonic acid (90percent pure) and 4 g of sulphuric acid are reacted with 207 g (1.06 mol) of benzotrichloride at 80° C. analogously to Example 3.

Yield: p-toluenesulphonyl chloride: 93.6percent; benzoyl chloride: 97.1percent; benzotrichloride: 2.2percent.

With sulfuric acid, toluene-4-sulfonic acid Patent; Bayer Aktiengesellschaft; US4349471; (1982); (A) English View in Reaxys

Cl

O S O

N

NH

S

O N

S N

O

N

N

S

Rx-ID: 2050913 View in Reaxys 90/135 Yield 60 %, 26 %

Conditions & References With thionyl chloride in dichloromethane, Time= 0.5h, T= 20 °C , other reagents (S2Cl2, SCl2) and time, Product distribution Bellesia, Franco; Grandi, Romano; Pagnoni, Ugo M.; Trave, Roberto; Gazzetta Chimica Italiana; vol. 111; nb. 7/8; (1981); p. 289 - 292 View in Reaxys O

O S N

NH

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

N O H 2N

Cl

S

O

Cl

N

S

S

S

O

O

N

N

Cl

Rx-ID: 2094290 View in Reaxys 91/135 Yield

Conditions & References

9 %, 85 %

With sulfur dichloride in dichloromethane, Time= 0.5h, T= 20 °C , other reagents (SOCl2, S2Cl2), products and time, Product distribution Bellesia, Franco; Grandi, Romano; Pagnoni, Ugo M.; Trave, Roberto; Gazzetta Chimica Italiana; vol. 111; nb. 7/8; (1981); p. 289 - 292 View in Reaxys

O S

N N H

O

O O

H 2N

Cl

S

Cl

H

O

NH

S O

S N

N

Rx-ID: 2135853 View in Reaxys 92/135 Yield 89 %

Conditions & References With disulfur dichloride in dichloromethane, Time= 0.5h, T= 20 °C , other reagents (SOCl2, SCl2) and time, Product distribution Bellesia, Franco; Grandi, Romano; Pagnoni, Ugo M.; Trave, Roberto; Gazzetta Chimica Italiana; vol. 111; nb. 7/8; (1981); p. 289 - 292 View in Reaxys O

O

N

S N

NH

N

N N

Cl

S S

O

S O

Rx-ID: 2178042 View in Reaxys 93/135 Yield 21 %, 61 %

Conditions & References With thionyl chloride, Time= 3h, T= 25 - 40 °C Zimmer, Oswald; Meier, Herbert; Chemische Berichte; vol. 114; nb. 9; (1981); p. 2938 - 2946 View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Cl

O S

S

O

N

O

NH

N

O

N S

Rx-ID: 2184254 View in Reaxys 94/135 Yield 55 %

Conditions & References With thionyl chloride in dichloromethane, Time= 0.75h, T= 20 °C , other reagents (SCl2, S2Cl2), products and time, Product distribution Bellesia, Franco; Grandi, Romano; Pagnoni, Ugo M.; Trave, Roberto; Gazzetta Chimica Italiana; vol. 111; nb. 7/8; (1981); p. 289 - 292 View in Reaxys

Cl O H 2N

O

Cl

S

O

S

N

S

N NH

N

O

O

O

S

Rx-ID: 2187168 View in Reaxys 95/135 Yield 80 %

Conditions & References With sulfur dichloride in dichloromethane, Time= 0.5h, T= 20 °C , other reagents (SOCl2, S2Cl2) and time, Product distribution Bellesia, Franco; Grandi, Romano; Pagnoni, Ugo M.; Trave, Roberto; Gazzetta Chimica Italiana; vol. 111; nb. 7/8; (1981); p. 289 - 292 View in Reaxys

Cl

Cl

O

S

O

S

N N H

O

O

S N

N

Rx-ID: 2189095 View in Reaxys 96/135 Yield 40 %

Conditions & References With thionyl chloride in dichloromethane, Time= 0.75h, T= 20 °C , other reagents (SCl2, S2Cl2) and time, Product distribution Bellesia, Franco; Grandi, Romano; Pagnoni, Ugo M.; Trave, Roberto; Gazzetta Chimica Italiana; vol. 111; nb. 7/8; (1981); p. 289 - 292 View in Reaxys O

O

N

S N

N

Cl

N

NH

N

S

O

S

S O

Rx-ID: 2838028 View in Reaxys 97/135 Yield

Conditions & References With thionyl chloride, Time= 3h, T= 25 - 40 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Zimmer, Oswald; Meier, Herbert; Chemische Berichte; vol. 114; nb. 9; (1981); p. 2938 - 2946 View in Reaxys N

O

O

N S

N

Cl

N

S

NH

N

O S

S O

Rx-ID: 3043225 View in Reaxys 98/135 Yield

Conditions & References

59 %, 20 %

With thionyl chloride, Time= 3h, T= 25 - 40 °C Zimmer, Oswald; Meier, Herbert; Chemische Berichte; vol. 114; nb. 9; (1981); p. 2938 - 2946 View in Reaxys O

O

Cl

O Cl

S

Cl

N

O S

N Cl

Cl

Cl Cl

Cl

N Cl

O

S

N O

Rx-ID: 3774369 View in Reaxys 99/135 Yield

Conditions & References T= 90.8 °C , other arylazo aryl sulfones, also with 1,1,2,2-tetrachloroethane, Rate constant, Mechanism Yoshida, Masato; Furuta, Naoki; Kobayashi, Michio; Bulletin of the Chemical Society of Japan; vol. 54; nb. 8; (1981); p.

2356 - 2359 View in Reaxys O

O

S

4-chloro-7-methoxy-cinnoline

NH

H 2N Cl O

S

monosodium-salt of/the/ 4-hydroxy-benzene-sulfonic acid-(1)

O

Rx-ID: 20661344 View in Reaxys 100/135 Yield

Conditions & References Reaction Steps: 2 1: 87 percent 2: SOCl2 / 3 h / 25 - 40 °C With thionyl chloride Zimmer, Oswald; Meier, Herbert; Chemische Berichte; vol. 114; nb. 9; (1981); p. 2938 - 2946 View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

O

O NH

O

Cl

O

O

O

N O

O

O

O

O OH

N

O

S

S

N

O

Rx-ID: 25347648 View in Reaxys 101/135 Yield

Conditions & References

73%

15 : cis-3-benzyloxy carbonylamino-4-oxo-2-azetidinylmethyl tosylate When cis-2-hydroxymethyl-1-(2,4-dimethoxybenzyl)-3-(4,5-diphenyl-2-oxo-4-oxazolin-3-yl)-4-oxoazetidine is reacted according to Example 13 except that mesyl chloride is substituted for p-toluenesulfonyl chloride, cis-3-(4,5-diphenyl-2-oxo-4-oxazolin-3-yl)-4-oxo-2-azetidinylmethyl mesylate is obtained; 73percent yield, mp 185°-8° from ethyl acetate-hexane.

Patent; SmithKline Corporation; US4103086; (1978); (A) English View in Reaxys Patent; SmithKline Corporation; US4072674; (1978); (A) English View in Reaxys Patent; SmithKline Corporation; US4166816; (1979); (A) English View in Reaxys Cl

toluene-4-sulfonic acid-hydrate

O

S O

Rx-ID: 5932814 View in Reaxys 102/135 Yield

Conditions & References With methyl-∼,∼-dichloromethyl ether, zinc(II) chloride Rieche; Gross; Chemische Berichte; vol. 92; (1959); p. 83,86,89 View in Reaxys Cl

N

N+

Cl –

O

S O

Rx-ID: 535024 View in Reaxys 103/135 Yield

Conditions & References With sulfur dioxide, copper(l) chloride, magnesium chloride Meerwein et al.; Chemische Berichte; vol. 90; (1957); p. 841,843 View in Reaxys

Cl

Cl S O

O O

OH O

S

O

S

O Cl

Rx-ID: 6208627 View in Reaxys 104/135 Yield

Conditions & References T= 0 °C , und 15grad, 30grad und 60grad Ognjanow; Sagorowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 29; (1956); p. 1299; engl. Ausg.

S. 1403

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

View in Reaxys

Cl S O

Cl

Cl

O

Al

OH O

Cl

O

S

Cl

O

S

O Cl

Rx-ID: 6208628 View in Reaxys 105/135 Yield

Conditions & References T= 15 °C Ognjanow; Sagorowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 29; (1956); p. 1299; engl. Ausg.

S. 1403 View in Reaxys

Cl S O

Cl

Cl

O

Fe

OH O

(v3)

Cl

O

Cl

S

O

S

O Cl

Rx-ID: 6208629 View in Reaxys 106/135 Yield

Conditions & References T= 15 °C Ognjanow; Sagorowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 29; (1956); p. 1299; engl. Ausg.

S. 1403 View in Reaxys Cl S

O

H N

O

OH O

O

NH 2

O

Cl O S

O

O

S

O Cl

Rx-ID: 6208630 View in Reaxys 107/135 Yield

Conditions & References T= 15 °C Ognjanow; Sagorowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 29; (1956); p. 1299; engl. Ausg.

S. 1403 View in Reaxys Cl S

O

mercury (II)-chloride

OH O

Cl O O

S

O

S

O Cl

Rx-ID: 6208631 View in Reaxys 108/135 Yield

Conditions & References T= 15 °C Ognjanow; Sagorowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 29; (1956); p. 1299; engl. Ausg.

S. 1403 View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Cl

Cl S O

O

sodium sulfate

OH O

O

S

O

S

O Cl

Rx-ID: 6208632 View in Reaxys 109/135 Yield

Conditions & References T= 65 °C Ognjanow; Sagorowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 29; (1956); p. 1299; engl. Ausg.

S. 1403 View in Reaxys Cl S

O

tin (II)-chloride

OH O

Cl O S

O

O

S

O Cl

Rx-ID: 6208633 View in Reaxys 110/135 Yield

Conditions & References T= 15 °C Ognjanow; Sagorowa; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 29; (1956); p. 1299; engl. Ausg.

S. 1403 View in Reaxys O

Cl O

S OH O

Cl OH

O

S HO

S OO

O

HO

S O

Rx-ID: 5932816 View in Reaxys 111/135 Yield

Conditions & References T= 0 °C Spryskow; Kus'mina; Zhurnal Obshchei Khimii; vol. 21; (1951); p. 714,716; engl.Ausg.S.787,788 View in Reaxys O Cl

O

S S

O

O

S O

O

Rx-ID: 750453 View in Reaxys 112/135 Yield

Conditions & References With chlorosulphuric acid, chloroform Huntress; Autenrieth; Journal of the American Chemical Society; vol. 63; (1941); p. 3446 View in Reaxys

O H S O

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aqueous hypochlorous acid

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Cl S

O

racemic (R)-1-phenyl-ethyl chloride

O

Rx-ID: 8286596 View in Reaxys 113/135 Yield

Conditions & References Houssa; Phillips; Journal of the Chemical Society; (1932); p. 1232,1234 View in Reaxys Cl

Cl

sodium-<toluene sulfonate-(4)> Cl Cl

O O

Cl

S O

Rx-ID: 5932818 View in Reaxys 114/135 Yield

Conditions & References T= 200 °C Patent; I.G. Farbenind.; DE574836; (1931); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 627 View in Reaxys Cl

Cl

H

Cl

Cl

HS

O

S O

Rx-ID: 5932806 View in Reaxys 115/135 Yield

Conditions & References Pollak; Riess; Monatshefte fuer Chemie; vol. 53/54; (1929); p. 98 View in Reaxys

S O

H 2N

O

O

O

S

Cl

O

NH

OH O

S HO

Cl O

S O

Rx-ID: 7446481 View in Reaxys 116/135 Yield

Conditions & References T= 20 °C Schuloff; Pollak; Riess; Chemische Berichte; vol. 62; (1929); p. 1855 View in Reaxys O S O

chloro water

Cl O

S

levorotatory 2-chloro-octane

O

Rx-ID: 8279086 View in Reaxys 117/135 Yield

Conditions & References

dl-p-toluenesulfinic acid d-octyl-(2)-ester Houssa; Kenyon; Phillips; Journal of the Chemical Society; (1929); p. 1710

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

View in Reaxys O S O

diluted hypochlorous acid

Cl O

S

p-toluenesulfonic acid d-octyl-(2)-ester

O

levorotatory 2-chloro-octane Rx-ID: 8285986 View in Reaxys 118/135 Yield

Conditions & References Produkt 5: l-Octanol-(2), dl-p-toluenesulfinic acid d-octyl-(2)-ester Houssa; Kenyon; Phillips; Journal of the Chemical Society; (1929); p. 1710 View in Reaxys

Cl

Cl

Cl H

H

Cl

O

Cl

Cl

HS

S

O

Cl

O

Rx-ID: 5932807 View in Reaxys 119/135 Yield

Conditions & References Patent; Chem. Fabr. v. Heyden; DE550685; (1928); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 531 View in Reaxys

Cl

H

H O

Cl

HS

Cl

O

S O

Rx-ID: 5932809 View in Reaxys 120/135 Yield

Conditions & References Patent; Chem. Fabr. v. Heyden; DE550685; (1928); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 531 View in Reaxys Cl

p-toluenesulfo fluoride

O

S O

Rx-ID: 5932811 View in Reaxys 121/135 Yield

Conditions & References With carbon disulfide, aluminium trichloride Steinkopf; Journal fuer Praktische Chemie (Leipzig); vol. <2> 117; (1927); p. 21 View in Reaxys With chlorosulfonic acid, T= 16 - 20 °C Steinkopf; Journal fuer Praktische Chemie (Leipzig); vol. <2> 117; (1927); p. 21 View in Reaxys O

Cl S

S

Al Cl

Cl

O

S

Cl O

F

S O

Rx-ID: 7446479 View in Reaxys 122/135

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Yield

Conditions & References T= 16 - 20 °C Steinkopf; Journal fuer Praktische Chemie (Leipzig); vol. <2> 117; (1927); p. 21 View in Reaxys Cl S

O

O

Cl Al

OH O

O

Cl

Cl

S

Cl

O

F

S O

Rx-ID: 7446480 View in Reaxys 123/135 Yield

Conditions & References T= 16 - 20 °C Steinkopf; Journal fuer Praktische Chemie (Leipzig); vol. <2> 117; (1927); p. 21 View in Reaxys Cl

pyrosulfuryl chloride

S

O

O

Rx-ID: 5932812 View in Reaxys 124/135 Yield

Conditions & References Steinkopf; Buchheim; Chemische Berichte; vol. 54; (1921); p. 2967 View in Reaxys

O O

O

S N–

Cl

H

N+ O

Cl S

O

<3-oxy-naphthoquinon-(1.4)-yl-(2)>-pyridinium betaine

O

Rx-ID: 8266626 View in Reaxys 125/135 Yield

Conditions & References Ullmann; Ettisch; Chemische Berichte; vol. 54; (1921); p. 271 View in Reaxys O

O

O

S O O

O O

S

Cl

S

O

HO

S O

Rx-ID: 625041 View in Reaxys 126/135 Yield

Conditions & References With thionyl chloride Meyer,H.; Schlegl; Monatshefte fuer Chemie; vol. 34; (1913); p. 576 View in Reaxys

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

Cl

O O

S

thionyl chloride ( impure )

O

S O

HO

Rx-ID: 5932813 View in Reaxys 127/135 Yield

Conditions & References Meyer,H.; Schlegl; Monatshefte fuer Chemie; vol. 34; (1913); p. 576 View in Reaxys O

O

S

thionyl chloride (pure )

HO

O

O

O

S

O O

S

Cl S

O

O

Rx-ID: 5932817 View in Reaxys 128/135 Yield

Conditions & References Meyer,H.; Schlegl; Monatshefte fuer Chemie; vol. 34; (1913); p. 576 View in Reaxys

O Cl

Cl

OH

HS

Cl

S

O

O

Rx-ID: 5932808 View in Reaxys 129/135 Yield

Conditions & References Zincke; Frohneberg; Chemische Berichte; vol. 42; (1909); p. 2722 Anm.; Chemische Berichte; vol. 43; (1910); p. 840 View in Reaxys Cl

Cl S O

O

OH O

S

o-toluenesulfonic acid chloride

O

Rx-ID: 6217793 View in Reaxys 130/135 Yield

Conditions & References T= 10 - 20 °C Gilliard, Monnet and Cartier; Chemiker-Zeitung, Chemische Apparatur; vol. 24; (1900); p. 800 View in Reaxys Patent; Gilliard, Monnet and Cartier; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 6; p. 1206 View in Reaxys Gilliard, Monnet and Cartier; Chem. Zentralbl.; vol. 69; nb. II; (1898); p. 743 View in Reaxys Patent; Gilliard, Monnet and Cartier; DE98030; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 4; p. 1261 View in Reaxys Cl

potassium salt of/the/ p-toluenesulfonic acid

O

S O

Rx-ID: 5932810 View in Reaxys 131/135 Yield

Conditions & References With phosphorus pentachloride, und Erhitzen Bourgeois; Recueil des Travaux Chimiques des Pays-Bas; vol. 18; (1899); p. 435

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4-Methylbenzenesulfonyl chloride (Tosyl chloride; TsCl) [C7H7ClO2S]

View in Reaxys Jaworski; ; (1865); p. 221 View in Reaxys Wolkowa; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 2; (1870); p. 169; ; (1870); p. 325 View in Reaxys O

O

S O

Cl

S

Cl

N

O

OH O

S

sulfate diethylamine

O

Rx-ID: 7458096 View in Reaxys 132/135 Yield

Conditions & References Patent; Marckwald; v.Droste-Huelshoff; DE105870 View in Reaxys Marckwald; v.Droste-Huelshoff; Chemische Berichte; vol. 31; (1898); p. 3262; Chem. Zentralbl.; vol. 71; nb. I; (1900); p. 524 View in Reaxys Cl

Cl Al

Cl

S O

Cl

Cl

O

O

O S

Cl

Cl

O

S O

Rx-ID: 5932815 View in Reaxys 133/135 Yield

Conditions & References Toehl; Eberhard; Chemische Berichte; vol. 26; (1893); p. 2942 View in Reaxys O

O

S

Cl

K+

chlorine

water

O

S–

S O

di-p-toluenesulfonyl sulfide di-p-toluenesulfonyl disulfide

di-p-toluenesulfonyl trisulfide Rx-ID: 8275443 View in Reaxys 134/135

Yield

Conditions & References Otto; Troeger; Chemische Berichte; vol. 24; (1891); p. 1138,1140 View in Reaxys Cl

O S

H

H O

Cl

Cl

HO

O

S O

Rx-ID: 6683010 View in Reaxys 135/135 Yield

Conditions & References Otto; v.Gruber; Justus Liebigs Annalen der Chemie; vol. 142; (1867); p. 93 View in Reaxys

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