2. Benzaldehyde to Benzonitrile [Reaxys, Reactions (35); 2013-06-14]

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35 reactions in Reaxys

2013-06-14 22h:27m:01s (EST)

Search as: As drawn, No salts, No mixtures

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Rx-ID: 601772 View in Reaxys 1/35 Yield 100 %

Conditions & References With anhydrous iron chloride, hydroxylamine hydrochloride in dimethyl sulfoxide, Molecular sieve Gowda, Ravikumar R.; Chakraborty, Debashis; European Journal of Organic Chemistry; nb. 12; (2011); p. 2226 2229 View in Reaxys

98 %

With oxygen, copper, ammonium chloride in pyridine, Time= 24h, T= 60 °C Capdevielle, Patrice; Lavigne, Andre; Maumy, Michel; Synthesis; nb. 6; (1989); p. 451 - 452 View in Reaxys

98 %

With hydroxylamine hydrochloride, toluene-4-sulfonic acid, Time= 0.00694444h, Microwave irradiation Reddy, M. B. Madhusudana; Pasha, M. A.; Synthetic Communications; vol. 40; nb. 22; (2010); p. 3384 - 3389 View in Reaxys

98 %

With (hydroxy(tosyloxy)iodo)benzene, ammonium acetate in water, acetonitrile, Time= 2h, T= 80 °C Zhu, Chenjie; Sun, Chengguo; Wei, Yunyang; Synthesis; nb. 24; (2010); p. 4235 - 4241; Art.No: F14610SS View in Reaxys

98 %

With hydroxylamine hydrochloride, zinc oxide, Time= 0.00972222h, Microwave irradiation, neat (no solvent) Madhusudana Reddy, M. B.; Pasha, M. A.; Chinese Chemical Letters; vol. 21; nb. 9; (2010); p. 1025 - 1028 View in Reaxys

96 %

With ammonia, iodine in tetrahydrofuran, water, Time= 0.5h, T= 20 °C Talukdar, Sanjay; Hsu, Jue-Liang; Chou, Tzu-Chi; Fang, Jim-Min; Tetrahedron Letters; vol. 42; nb. 6; (2001); p.

1103 - 1106 View in Reaxys

94 %

With aluminium trichloride, sodium azide in tetrahydrofuran, Time= 21h, Heating Suzuki, Hitomi; Nakaya, Chie; Synthesis; nb. 7; (1992); p. 641 - 642 View in Reaxys

94 %

With XY-zeolite, hydroxylamine hydrochloride, Time= 0.0166667h, microwave irradiation Srinivas, K. V. N. S.; Reddy, E. Bolla; Das, Biswanath; Synlett; nb. 4; (2002); p. 625 - 627 View in Reaxys

93 %

With 1-methyl-pyrrolidin-2-one, hydroxylamine hydrochloride, Time= 0.0833333h, T= 200 °C , microwave irradiation Koshima, Hideko; Hamada, Mitsuo; Tani, Makiko; Iwasaki, Shunsuke; Sato, Fumika; Heterocycles; vol. 57; nb.

11; (2002); p. 2145 - 2148 View in Reaxys

93 %

With [bis(acetoxy)iodo]benzene, ammonium acetate, sodium lauryl sulfate in water, Time= 2h, T= 70 °C Zhu, Chenjie; Ji, Lei; Wei, Yunyang; Synthesis; nb. 18; (2010); p. 3121 - 3125 View in Reaxys

93 %

Example Title 13 A typical method for preparation of nitrile from aldehyde using AHA: General procedure: 4-Isopropylbenzaldehyde 1a (0.50 g, 3.37 mmol), acetohydroxamic acid (0.30 g, 4.05 mmol), acetonitrile (5 ml), and Bi(OTf)3 (0.11 g, 0.17 mmol) were taken into a 25 ml round-bottomed flask fitted with a condenser and calcium chloride guard tube. The mixture was refluxed for 14 h and after completion of the reaction (GC, 10percent SE-30 on Chromosorb, 10' .x. 1/8 column), the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude product obtained was purified by normal column chromatography(silica gel 100-200 mesh, ethyl acetate/hexane = 1:20) to obtain 4-isopropylbenzonitrile 3a (0.47 g, 97percent).

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With bismuth trifluoromethanesulphonate, methanecarbohydroxamic acid in acetonitrile, Time= 15h, Reflux Sridhar, Madabhushi; Reddy, Mallu Kishore Kumar; Sairam, Vangipuram Venkata; Raveendra, Jillella; Godala, Kondal Reddy; Narsaiah, Chinthala; Ramanaiah, Beeram China; Reddy, Cirandur Suresh; Tetrahedron Letters; vol. 53; nb. 27; (2012); p. 3421 - 3424 View in Reaxys 92 %

With hydroxylamine hydrochloride, tetrachlorosilane, Time= 0.0166667h, T= 105 °C , microwave irradiation Srinivas, K. V. N. S.; Mahender, I.; Das, Biswanath; Chemistry Letters; vol. 32; nb. 8; (2003); p. 738 - 739 View in Reaxys

92 %

With ammonium hydroxide, bis-[(trifluoroacetoxy)iodo]benzene in water, Time= 0.5h, T= 25 °C Telvekar, Vikas N.; Rane, Rajesh A.; Namjoshi, Tejal V.; Synthetic Communications; vol. 40; nb. 4; (2010); p. 494 - 497 View in Reaxys

92 %

With tert.-butylhydroperoxide, ammonium hydroxide, tetra-(n-butyl)ammonium iodide in water, Time= 12h, T= 80 °C , Catalytic behavior, Concentration, Temperature, Reagent/catalyst Wang, Liang; Shen, Chen; Wang, Hai-Ping; Zhou, Wei-You; Sun, Fu-An; He, Ming-Yang; Chen, Qun; ; vol. 36; nb. 8; (2012); p. 460 - 462,3 View in Reaxys

91 %

With potassium hydroxide, ammonium hydrogen carbonate, ((n-Bu)4N)2S2O8, copper(I) formate, nickel(II) formate in acetonitrile, Time= 2h, T= 20 °C , Condensation, Oxidation Chen, Fen-Er; Fu, Han; Meng, Ge; Cheng, Yu; Lue, Yin-Xiang; Synthesis; nb. 11; (2000); p. 1519 - 1520 View in Reaxys

90 %

With PhNHCO2NH2*TsOH in toluene, Time= 0.5h, Heating, Condensation, elimination Coskun, Necdet; Arikan, Nevin; Tetrahedron; vol. 55; nb. 40; (1999); p. 11943 - 11948 View in Reaxys

90 %

With hydroxylamine hydrochloride, carbon, methanesulfonyl chloride, Time= 1.5h, T= 100 °C Sharghi, Hashem; Sarvari, Mona Hosseini; Synthesis; nb. 2; (2003); p. 243 - 246 View in Reaxys

90 %

With ammonium hydroxide, ammonium cerium(IV) nitrate, Time= 0.25h, T= 0 °C Bandgar, B. P.; Makone, S. S.; Synlett; nb. 2; (2003); p. 262 - 264 View in Reaxys

90 %

With ammonium hydroxide, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in acetonitrile, Time= 2h, T= 20 °C Arote, Nitin D.; Bhalerao, Dinesh S.; Akamanchi, Krishnacharya G.; Tetrahedron Letters; vol. 48; nb. 21; (2007); p. 3651 - 3653 View in Reaxys

90 %

With ammonium hydroxide, Time= 4h, T= 25 °C Telvekar, Vikas N.; Patel, Kavit N.; Kundaikar, Harish S.; Chaudhari, Hemchandra K.; Tetrahedron Letters; vol.

49; nb. 14; (2008); p. 2213 - 2215 View in Reaxys

90 %

With trichloroisocyanuric acid, ammonia in water, T= 20 - 60 °C Veisi, Hojat; Synthesis; nb. 15; (2010); p. 2631 - 2635; Art.No: Z04110SS View in Reaxys

90 %

With hydroxylamine hydrochloride, iron(II) sulfate in N,N-dimethyl-formamide, Time= 3.5h, Reflux Patil, Dinanath D.; Wadhava, Gurumeet C.; Deshmukh, Arun K.; Asian Journal of Chemistry; vol. 24; nb. 3; (2012); p. 1401 - 1402

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View in Reaxys 89 %

With ammonia, aluminum oxide, copper, Time= 0.000555556h, T= 300 °C , p= 760Torr Card, Roger J.; Schmitt, J. Lawrence; Journal of Organic Chemistry; vol. 46; (1981); p. 754 - 757 View in Reaxys

89 %

With manganese(IV) oxide, ammonia, magnesium sulfate in tetrahydrofuran, isopropyl alcohol, Time= 16h, T= 20 °C Lai, Gaifa; Bhamare, Nana K.; Anderson, Wayne K.; Synlett; nb. 2; (2001); p. 230 - 231 View in Reaxys

89 %

Stage 1: With ammonia in water, Time= 0.166667h, T= 20 °C Stage 2: With tetra-n-butylammonium tribromide in water, Time= 2h, T= 20 °C Zhu, Yi-Zhong; Cai, Chun; Monatshefte fuer Chemie; vol. 141; nb. 6; (2010); p. 637 - 639 View in Reaxys

87 %

General procedure for the synthesis of nitriles: A pressure tube was charged with an appropriate amount of Zn(OTf)2 (0.036 mmol, 5.0 mol percent), the corresponding aldehyde (0.72 mmol) and hydroxylamine hydrochloride (1.2 equiv, 0.86 mmol). After the addition of toluene (2.0 mL) the reaction mixture was stirred in a preheated oil bath at 100 °C for 24 h. The mixture was cooled in an ice bath and biphenyl (internal standard) was added. The solution was diluted with dichloromethane and an aliquot was taken for GC-analysis (30 m Rxi-5 ms column, 40-300 °C). The solvent was carefully removed and the residue was purified by column chromatography (n-hexane/ethyl acetate). The analytical properties of the corresponding nitriles are in agreement with the literature.

With Zn(ClO4)2*6H2O, hydroxylamine hydrochloride in toluene, Time= 24h, T= 100 °C Enthaler, Stephan; Weidauer, Maik; Schroeder, Fanny; Tetrahedron Letters; vol. 53; nb. 7; (2012); p. 882 - 885 View in Reaxys

86 %

With hydroxylamine hydrochloride in various solvent(s), Time= 5h, T= 110 - 115 °C Kumar, H. M. Sampath; Reddy, B. V. Subba; Reddy, P. Tirupathi; Yadav, J. S.; Synthesis; nb. 4; (1999); p. 586 587 View in Reaxys

84 %

With Ph2S=NH in benzene, Time= 24h, Heating Gelas-Mialhe, Yvonne; Vessiere, Roger; Synthesis; nb. 12; (1980); p. 1005 - 1007 View in Reaxys

84 %

With sodium hydrogen sulphate, hydroxylamine hydrochloride, silica gel, Time= 0.0333333h, microwave irradiation, Condensation, Dehydration Das, Biswanath; Madhusudhan, P.; Venkataiah, B.; Synlett; nb. 10; (1999); p. 1569 - 1570 View in Reaxys

84 %

With phthalic anhydride, hydroxylamine hydrochloride, triethylamine, Time= 0.05h, Irradiation, Reduction Veverkova, Eva; Toma, Stefan; Synthetic Communications; vol. 30; nb. 17; (2000); p. 3109 - 3114 View in Reaxys

83 %

With pyridine, hydroxylamine hydrochloride, 1.) 10 min, 2.) toluene, 3 h, reflux Saednya, Akbar; Synthesis; nb. 3; (1982); p. 190 - 191 View in Reaxys

83 %

With hydroxylamine hydrochloride, sodium iodide in acetonitrile, Time= 2.16667h, Heating Ballini, Roberto; Fiorini, Dennis; Palmieri, Alessandro; Synlett; nb. 12; (2003); p. 1841 - 1843 View in Reaxys

82 %

With sodium azide, trifluorormethanesulfonic acid in acetonitrile, Time= 0.0333333h, T= 20 °C , Schmidt reaction Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Journal of Organic Chemistry; vol. 77; nb. 12; (2012); p. 5364 5370

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View in Reaxys 81 %

With boron trifluoride diethyl etherate, O-(2-aminobenzoyl) hydroxylamine in ethanol, Time= 4h, Heating Reddy, P.S.N.; Reddy, P.Pratar; Synthetic Communications; vol. 18; nb. l6-17; (1988); p. 2179 - 2182 View in Reaxys

81 %

To a mixture of aldehyde (1 mmol) and aq. ammonia (3 mL), CAN/KI or CeCl3·7H2O/KI in hydrogenperoxide (3 mL) or CeCl3·7H2O/KI in urea hydrogen peroxide (3 mmol) was added. The resulting mixture was stirred in sealed tube at room temperature or 60 °C. After completion of the reaction, the reaction mixture was diluted with water and Na2S2O3 (5 mmol) was added. Finally product extracted with dichloromethane (20 mL) and organic phase dried over Na2SO4 (3 g). After evaporation of dichloromethane, corresponding nitrile was obtained in good yield.

With ammonium hydroxide, cerium(III) chloride heptahydrate, dihydrogen peroxide, potassium iodide, Time= 4h, T= 60 °C , Reagent/catalyst, Time Hajjami, Maryam; Ghorbani-Choghamarani, Arash; Gholamian, Fatemeh; Zolfigol, Mohammad Ali; Chinese Chemical Letters; vol. 23; nb. 12; (2012); p. 1323 - 1326,4 View in Reaxys

80 %

With 1-nitroethane, pyridine hydrochloride, Time= 1h, Heating Dauzonne, Daniel; Demerseman, Pierre; Royer, Rene; Synthesis; nb. 9; (1981); p. 739 - 740 View in Reaxys

78 %

With ammonium hydroxide, periodic acid, potassium iodide, Time= 65745h, T= 60 °C , Sealed tube, Green chemistry Ghorbani-Choghamarani, Arash; Sardari, Sara; Zolfigol, Mohammad Ali; Hajjami, Maryam; Synthetic Communications; vol. 43; nb. 1; (2013); p. 52 - 58,7 View in Reaxys

77 %

With aluminum oxide, Oxonereg;, hydroxylamine hydrochloride in solid, Time= 0.125h, microwave irradiation Bose, D. Subhas; Narsaiah, A. Venkat; Tetrahedron Letters; vol. 39; nb. 36; (1998); p. 6533 - 6534 View in Reaxys

74 %

With hydroxylamine hydrochloride in dimethyl sulfoxide, Time= 1h, T= 100 °C Chill, Samuel T.; Mebane, Robert C.; Synthetic Communications; vol. 39; nb. 20; (2009); p. 3601 - 3606 View in Reaxys

73 %

With methanol, ammonia, sodium methylate, potassium iodide, T= 5 °C , electrooxidation, other aliphatic, aromatic aldehydes, Mechanism Okimoto, Mitsuhiro; Chiba, Toshiro; Journal of Organic Chemistry; vol. 53; nb. 1; (1988); p. 218 - 219 View in Reaxys

73 %

With ammonia, sodium methylate in methanol, T= 5 °C , electrooxidation Okimoto, Mitsuhiro; Chiba, Toshiro; Journal of Organic Chemistry; vol. 53; nb. 1; (1988); p. 218 - 219 View in Reaxys

67 %

With hydroxylamine hydrochloride, ammonium acetate, Time= 0.0333333h, Microwave irradiation, Neat (no solvent) Rezaei, Ramin; Rastin, Nedaa; Mohammadi, Mohammad Kazem; Chinese Journal of Chemistry; vol. 28; nb. 6; (2010); p. 993 - 996 View in Reaxys

67 %

With ammonium hydroxide, sodium periodate, potassium iodide, Time= 1.5h, T= 60 °C Zolfigol, Mohammad Ali; Hajjami, Maryam; Ghorbani-Choghamarani, Arash; Bulletin of the Korean Chemical Society; vol. 32; nb. 12; (2011); p. 4191 - 4194 View in Reaxys

65.8 %

With Ph2S=NH in benzene, Time= 5h, T= 80 °C

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Furukawa, Naomichi; Fukumura, Mitsuo; Akasaka, Takeshi; Yoshimura, Toshiaki; Oae, Shigeru; Tetrahedron Letters; vol. 21; (1980); p. 761 - 762 View in Reaxys 62 %

With trimethylsilylazide, zinc(II) chloride in dichloromethane, Time= 4h, Ambient temperature, var. temp.

Nishiyama, Kozaburo; Watanabe, Akio; Chemistry Letters; (1984); p. 773 - 774 View in Reaxys

50 %

With Mexican Bentonite, hydroxylamine hydrochloride, Time= 0.25h, Irradiation Delgado, F.; Cano, A.C.; Garcia, O.; Alvarado, J.; Velasco, L.; et al.; Synthetic Communications; vol. 22; nb. 14; (1992); p. 2125 - 2128 View in Reaxys

50 %

With pyridine, hydroxylamine hydrochloride, formamide in xylene, Time= 6h, Heating, Condensation Ali, Sayyed Iliyas; Nikalje, Milind D.; Dewkar, Gajanan K.; Paraskar, Abhimanyu S.; Jagtap, H. S.; Sudalai, A.; Journal of Chemical Research, Synopses; nb. 1; (2000); p. 30 - 31 View in Reaxys

24 %

With ammonium hydroxide, dihydrogen peroxide, copper dichloride in isopropyl alcohol, T= 17 - 30 °C , oxidative dehydrogenation Erman, Mark B.; Snow, Joe W.; Williams, Melissa J.; Tetrahedron Letters; vol. 41; nb. 35; (2000); p. 6749 - 6752 View in Reaxys T= 355 - 415 °C , Leiten im Gemisch mit Ammoniak ueber einen Kupfer-Aluminiumoxid-Katalysator Patent; Phillips Petr. Co.; US2525818; (1946) View in Reaxys With titanium vanadium oxide, ammonia, T= 350 - 420 °C Kargarlizkii et al.; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 32; (1959); p. 388,390; engl.

Ausg. S. 404 View in Reaxys Kagarliszkii; Suworow; ; nb. 1; (1958); p. 84; ; (1959); p. 14043 View in Reaxys With tin vanadium oxide, ammonia, T= 350 - 420 °C Kargarlizkii et al.; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 32; (1959); p. 388,390; engl.

Ausg. S. 404 View in Reaxys Kagarliszkii; Suworow; ; nb. 1; (1958); p. 84; ; (1959); p. 14043 View in Reaxys With tris-(2-chloro-ethyl)-amine, sulfuric acid, benzene Houff; Journal of Organic Chemistry; vol. 22; (1957); p. 344 View in Reaxys With ammonia, T= 420 - 440 °C , beim Ueberleiten ueber Thoriumoxyd Mailhe; de Godon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 166; (1918); p.

216; Bulletin de la Societe Chimique de France; vol. <4>23; (1918); p. 239 View in Reaxys Mailhe; Annales de Chimie (Cachan, France); vol. <9>13; (1920); p. 210; ; vol. 15; p. 9550; Chem. Zentralbl.; vol. 91; nb. I; (1920); p. 115 View in Reaxys With hydrogenchloride, hydrogen azide Patent; Knoll and Co., Schmidt; DE455585; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 2862 View in Reaxys

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With carbon disulfide, sodium hydroxide, hydroxylamine hydrochloride, tetra(n-butyl)ammonium hydrogensulfate, 1) benzene, 0.5 h, room temp.; 2) benzene, room temp., 2 h, Yield given. Multistep reaction Shinozaki, Hiraku; Imaizumi, Mari; Tajima, Moritaka; Chemistry Letters; (1983); p. 929 - 932 View in Reaxys 74 % Chro- With sulfur, ammonia, sodium nitrite, Time= 4h, T= 100 °C mat.

Sato, Ryu; Ityoh, Kaoru; Itoh, Kazumi; Nishina, Hironori; Goto, Takehiko; Saito, Minoru; Chemistry Letters; (1984); p. 1913 - 1916 View in Reaxys With ammonia, oxygen, copper(l) chloride in pyridine, Ambient temperature Demmin,T.R.; Swerdloff,M.D.; Rogic,M.M.; Journal of the American Chemical Society; vol. 103; (1981); p. 5795 View in Reaxys 75 % Chro- With formic acid, hydroxylamine hydrochloride, silica gel, Time= 0.05h, Irradiation mat.

Feng, Jun-Cai; Liu, Bin; Dai, Li; Bian, Ning-Sheng; Synthetic Communications; vol. 28; nb. 20; (1998); p. 3765 3768 View in Reaxys With hydroxylamine hydrochloride, ethyl phosphorodichloridate, 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane, Time= 15h, T= 20 °C , Product distribution, Further Variations: Reagents Zhu, Jia-Liang; Lee, Fa-Yen; Wu, Jen-Dar; Kuo, Chun-Wei; Shia, Kak-Shan; Synlett; nb. 8; (2007); p. 1317 - 1319 View in Reaxys Reaction Steps: 2 1: 48 percent / sodium acetate / ethanol 2: 67 percent / LDA / tetrahydrofuran / -80 °C With sodium acetate, lithium diisopropyl amide in tetrahydrofuran, ethanol Konakahara, Takeo; Matsuki, Masayuki; Sugimoto, Shinji; Sato, Kenji; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1987); p. 1489 - 1494 View in Reaxys Reaction Steps: 3 1: benzene / Heating 2: methanol / 4 h / Heating 3: sodium methoxide / methanol / 25 °C / reagent concentration dependence (for methoxide); or triethylamine, pyrrolidine, N-methylpiperidine, morpholine, N-ethylmorpholine, and N-methylmorpholine With sodium methylate in methanol, benzene Nguyen, Minh Tho; Clarke, Leo F.; Hegarty, Anthony F.; Journal of Organic Chemistry; vol. 55; nb. 25; (1990); p.

6177 - 6183 View in Reaxys Example Name 9 An operation was conducted in the same manner as in Example 8 except that benzyl alcohol was replaced by 0.42 g (4 mmol) of benzaldehyde and sodium bromate was used by 0.2 g (1.35 mmol). The reaction mixture contained, as a component, >99.9percent (in terms of areal ratio of gas chromatography) of benzonitrile. Gas mass chromatography (GC-MS) was conducted and the molecular ion peak [M+] of benzonitrile was confirmed to be 103.

With Sodium bromate, ammonia, acetic acid in water, Time= 15h, T= 90 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1555257; (2005); (A1) English View in Reaxys Example Name 14 An operation was conducted in the same manner as in Example 9 except that sodium bromate was replaced by 0.27 g (2 mmol) of sodium bromite. The reaction mixture contained, as components, 79.0percent (in terms of areal ratio of gas chromatography) of benzonitrile and 17.3percent of benzaldehyde. Gas mass chromatography (GC-MS) was conducted and the molecular ion peak [M+] of benzonitrile was confirmed to be 103.

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With sodium bromite, ammonia, acetic acid in water, Time= 15h, T= 90 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1555257; (2005); (A1) English View in Reaxys Example Name 17 An operation was conducted in the same manner as in Example 9 except that acetic acid was replaced by 2 ml (21.9 mmol) of n-butanoic acid. The reaction mixture contained, as components, 92.8percent (in terms of areal ratio of gas chromatography) of benzonitrile and 7.2percent of benzaldehyde. Gas mass chromatography (GC-MS) was conducted and the molecular ion peak [M+] of benzonitrile was confirmed to be 103.

With Sodium bromate, ammonia, butyric acid in water, Time= 15h, T= 90 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1555257; (2005); (A1) English View in Reaxys Example Name 16 An operation was conducted in the same manner as in Example 9 except that acetic acid was replaced by 2 ml (26.8 mmol) of propionic acid. The reaction mixture contained, as components, 92.1percent (in terms of areal ratio of gas chromatography) of benzonitrile and 6.4percent of benzaldehyde. Gas mass chromatography (GC-MS) was conducted and the molecular ion peak [M+] of benzonitrile was confirmed to be 103.

With Sodium bromate, ammonia, propionic acid in water, Time= 15h, T= 90 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1555257; (2005); (A1) English View in Reaxys Example Name 15 An operation was conducted in the same manner as in Example 9 except that sodium bromate was replaced by 0.23 g (1.35 mmol) of potassium bromate. The reaction mixture contained, as components, 88.2percent (in terms of areal ratio of gas chromatography) of benzonitrile and 7.4percent of benzaldehyde. Gas mass chromatography (GC-MS) was conducted and the molecular ion peak [M+] of benzonitrile was confirmed to be 103.

With KBrO3, ammonia, acetic acid in water, Time= 15h, T= 90 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1555257; (2005); (A1) English View in Reaxys With tert.-butylhydroperoxide, ammonia, potassium iodide in water, Time= 8h, T= 60 °C Rajender Reddy, K.; Uma Maheswari, C.; Venkateshwar, M.; Prashanthi, S.; Lakshmi Kantam, M.; Tetrahedron Letters; vol. 50; nb. 18; (2009); p. 2050 - 2053 View in Reaxys With ammonia, iodine in tetrahydrofuran, water, T= 20 °C Jadhav, Ganesh R.; Shaikh, Mohammad U.; Kale, Rajesh P.; Ghawalkar, Anand R.; Gill, Charansingh H.; Journal of Heterocyclic Chemistry; vol. 46; nb. 5; (2009); p. 980 - 987 View in Reaxys With ammonia, iodine in tetrahydrofuran, water, Time= 1h, T= 20 °C Reddy, M. B. Madhusudana; Pasha, M. A.; Synthetic Communications; vol. 41; nb. 14; (2011); p. 2081 - 2085 View in Reaxys Reaction Steps: 2 1: hydroxylamine hydrochloride; sodium carbonate / methanol; water / Reflux 2: acetic anhydride / Reflux With hydroxylamine hydrochloride, acetic anhydride, sodium carbonate in methanol, water Li, Ziyuan; Ma, Ling; Xu, Jinyi; Kong, Lingyi; Wu, Xiaoming; Yao, Hequan; Chemical Communications (Cambridge, United Kingdom); vol. 48; nb. 31; (2012); p. 3763 - 3765 View in Reaxys Reaction Steps: 2 1: sodium tetrahydroborate

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2: Cu(ClO4)2*6H2O; trimethylsilylazide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,2-dichloro-ethane / 3 h / 60 °C With sodium tetrahydroborate, Cu(ClO4)2*6H2O, trimethylsilylazide, 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,2dichloro-ethane Rokade, Balaji V.; Malekar, Sanjeev K.; Prabhu, Kandikere Ramaiah; Chemical Communications (Cambridge, United Kingdom); vol. 48; nb. 44; (2012); p. 5506 - 5508 View in Reaxys Reaction Steps: 2 1: methanecarbohydroxamic acid; boron trifluoride diethyl etherate / methanol / Reflux 2: bismuth trifluoromethanesulphonate / acetonitrile / 8 h / Reflux With bismuth trifluoromethanesulphonate, methanecarbohydroxamic acid, boron trifluoride diethyl etherate in methanol, acetonitrile Sridhar, Madabhushi; Reddy, Mallu Kishore Kumar; Sairam, Vangipuram Venkata; Raveendra, Jillella; Godala, Kondal Reddy; Narsaiah, Chinthala; Ramanaiah, Beeram China; Reddy, Cirandur Suresh; Tetrahedron Letters; vol. 53; nb. 27; (2012); p. 3421 - 3424 View in Reaxys With manganese(IV) oxide, oxygen, urea in 1,4-dioxane, water, Time= 2h, T= 140 °C , p= 3800.26Torr Wang, Ye; Yamaguchi, Kazuya; Mizuno, Noritaka; Angewandte Chemie, International Edition; vol. 51; nb. 29; (2012); p. 7250 - 7253; Angewandte Chemie; vol. 124; nb. 29; (2012); p. 7362 - 7365 View in Reaxys 100 %Spectr.

With [BMIM(SO3H)][OTf], trimethylsilylazide, 1-n-butyl-3-methylimidazolium hexafluorophosphate, Time= 3h, T= 20 50 °C , Sonication, Schmidt Reaction, Time, Reagent/catalyst Nandi, Ganesh C.; Laali, Kenneth K.; Tetrahedron Letters; vol. 54; nb. 17; (2013); p. 2177 - 2179,3 View in Reaxys H

O N

O

O

N

O

N O

E

HO

O

N

Rx-ID: 2677944 View in Reaxys 2/35 Yield

Conditions & References

76 %

With ammonium acetate in acetic acid, Time= 3h, T= 50 °C , p= 7500600Torr Agafonov, N. E.; Sedishev, I. P.; Dudin, A. V.; Kutin, A. A.; Stashina, G. A.; Zhulin, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 40; nb. 2.2; (1991); p. 366 - 372; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 2; (1991); p. 426 - 433 View in Reaxys With ammonium acetate in acetic acid, Time= 3h, T= 50 °C , p= 7500600Torr Agafonov, N. E.; Sedishev, I. P.; Dudin, A. V.; Kutin, A. A.; Stashina, G. A.; Zhulin, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 40; nb. 2.2; (1991); p. 366 - 372; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 2; (1991); p. 426 - 433 View in Reaxys

H

N

O

N N N

N NH 2

Rx-ID: 2690762 View in Reaxys 3/35 Yield 75 %, 2 %

Conditions & References With trimethylsilylacetylene, zinc(II) chloride in chloroform, Time= 4h, Ambient temperature Nishiyama, Kozaburo; Oba, Makoto; Watanabe, Akio; Tetrahedron; vol. 43; nb. 4; (1987); p. 693 - 700 View in Reaxys

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9/19

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H

N

O HO

N

Rx-ID: 8566740 View in Reaxys 4/35 Yield

Conditions & References

Ca. 30 %, 65 %

With hydroxylamine hydrochloride, palladium diacetate, caesium carbonate in dimethyl sulfoxide, Time= 15h, T= 100 °C , Molecular sieve Ali, Md. Ashif; Punniyamurthy, Tharmalingam; Advanced Synthesis and Catalysis; vol. 352; nb. 2-3; (2010); p. 288 - 292 View in Reaxys

72 % Chro- With hydroxylamine hydrochloride, FeOO280 in toluene, Time= 4h, Heating, Condensation, dehydration mat., 28 % Bajpai, Anu R.; Deshpande, Abhay B.; Samant, Shriniwas D.; Synthetic Communications; vol. 30; nb. 15; (2000); Chromat. p. 2785 - 2792 View in Reaxys H

N

O

H 2N O

Rx-ID: 9198551 View in Reaxys 5/35 Yield

Conditions & References

79 %, 8 With [Ru(η6-C6Me6)Cl2(tris(dimethylamino)phosphine)], hydroxylamine hydrochloride, sodium hydrogencarbonate in %Chromat. water, Time= 7h, T= 100 °C , Inert atmosphere, Sealed tube, Green chemistry, Concentration, Reagent/catalyst, Solvent, Temperature, Time Garcia-Alvarez, Rocio; Diaz-Alvarez, Alba E.; Crochet, Pascale; Cadierno, Victorio; RSC Advances; vol. 3; nb.

17; (2013); p. 5889 - 5894,6 View in Reaxys With hydroxylamine hydrochloride, methanesulfonyl chloride, Time= 5h, T= 100 °C , Title compound not separated from byproducts Sharghi, Hashem; Sarvari, Mona Hosseini; Synthesis; nb. 2; (2003); p. 243 - 246 View in Reaxys H

N

O HO

Rx-ID: 23483590 View in Reaxys 6/35 Yield

Conditions & References Example Name 19 Into a 15 ml, test tube-shaped reactor equipped with a magnetic stirrer and a reflux condenser were added 0.22 g (2 mmol) of benzyl alcohol, 0.21 g (2 mmol) of benzaldehyde, 0.30 g (2 mmol) of sodium bromate, 2 ml (34.8 mmol) of acetic acid and 0.4 g (5.9 mmol) of 25percent aqueous ammonia, followed by stirring at 90°C for 3 hours. The reaction mixture contained, as a product, 94.6percent (in terms of areal ratio of gas chromatography) of benzonitrile, and benzaldehyde remained by 4.4percent. Gas mass chromatography (GC-MS) was conducted and the molecular ion peak [M+] of benzonitrile was confirmed to be 103.

With Sodium bromate, ammonia, acetic acid in water, Time= 3h, T= 90 °C , Product distribution / selectivity Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1555257; (2005); (A1) English View in Reaxys

Copyright © 2013 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

10/19

2013-06-14 22:30:07

H

N

O

(C5H5)2(Cl)Zr{trans-CH=CH[CH2]4OSi(CH3)2(tBu)}

iBu3Al Rx-ID: 14883414 View in Reaxys 7/35

Yield

Conditions & References Reaction Steps: 2 1: polymer-supported hydrazine / CH2Cl2 / 1 h / 20 °C 2: 0.049 mg / mCPBA; NaHCO3 / CH2Cl2 / 1 h / 20 °C With polymer-supported hydrazine, sodium hydrogencarbonate, 3-chloro-benzenecarboperoxoic acid in dichloromethane Baxendale, Ian R.; Ley, Steven V.; Sneddon, Helen F.; Synlett; nb. 5; (2002); p. 775 - 777 View in Reaxys Reaction Steps: 2 1: 100 percent / NH2OH*HCl; pyridine / ethanol 2: 94 percent / [RuCl2(p-cymene)]2; 4 Angstroem molecular sieves / acetonitrile / 0.17 h / 80 °C With pyridine, [(η6-para-cymene)RuCl2]2, 4 A molecular sieve, hydroxylamine hydrochloride in ethanol, acetonitrile Yang, Soon Ha; Chang, Sukbok; Organic Letters; vol. 3; nb. 26; (2001); p. 4209 - 4212 View in Reaxys Reaction Steps: 2 1: ammonia (g) / CuCl2 / propan-2-ol / 2.5 h / 17 - 30 °C 2: aq. H2O2 / 4 h With ammonia, dihydrogen peroxide, copper dichloride in isopropyl alcohol, 1: Condensation / 2: oxidative dehydrogenation Erman, Mark B.; Snow, Joe W.; Williams, Melissa J.; Tetrahedron Letters; vol. 41; nb. 35; (2000); p. 6749 - 6752 View in Reaxys H

N

O

Fmoc-L-tert-leucine on Wang resin

Rx-ID: 11332885 View in Reaxys 8/35 Yield

Conditions & References Reaction Steps: 2 1: Xantphos / Ru(CO)(PPh3)3H2 / toluene / 24 h / Heating With 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene, Ru(CO)(PPh3)3H2 in toluene Anand, Naveen; Owston, Nathan A.; Parker, Alexandra J.; Slatford, Paul A.; Williams, Jonathan M. J.; Tetrahedron Letters; vol. 48; nb. 44; (2007); p. 7761 - 7763 View in Reaxys Reaction Steps: 2 1: Xantphos / Ru(CO)(PPh3)3H2 / toluene / 24 h / Heating With 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene, Ru(CO)(PPh3)3H2 in toluene Anand, Naveen; Owston, Nathan A.; Parker, Alexandra J.; Slatford, Paul A.; Williams, Jonathan M. J.; Tetrahedron Letters; vol. 48; nb. 44; (2007); p. 7761 - 7763 View in Reaxys H

N O

O HO

Rx-ID: 2690840 View in Reaxys 9/35

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11/19

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Yield

Conditions & References

82.2 %, 10.8 %

With ammonium hydroxide, dipotassium peroxodisulfate, copper(II) nitrate, Time= 15h, T= 25 °C , variation of conditions (other oxidizing agent: O2, cosolvent MeCN); other carbonyl compounds, Product distribution Arora, Pramod K.; Sayre, Lawrence M.; Tetrahedron Letters; vol. 32; nb. 8; (1991); p. 1007 - 1010 View in Reaxys

10.8 %, 82.2 %

With ammonium hydroxide, dipotassium peroxodisulfate, copper(II) nitrate, Time= 15h, T= 25 °C Arora, Pramod K.; Sayre, Lawrence M.; Tetrahedron Letters; vol. 32; nb. 8; (1991); p. 1007 - 1010 View in Reaxys

9 %, 76 % Chromat.

With nickel sulphate, ammonium hydroxide, sodium hydroxide, dipotassium peroxodisulfate in water, Time= 3h, Ambient temperature Yamazaki, Shigakazu; Yamazaki, Yasuyuki; Chemistry Letters; nb. 4; (1990); p. 571 - 574 View in Reaxys

76 % Chro- With nickel sulphate, ammonium hydroxide, sodium hydroxide, dipotassium peroxodisulfate in water, Time= 3h, Ammat., 9 % bient temperature Yamazaki, Shigakazu; Yamazaki, Yasuyuki; Chemistry Letters; nb. 4; (1990); p. 571 - 574 View in Reaxys 76 % Chro- With nickel sulphate, ammonium hydroxide, sodium hydroxide, dipotassium peroxodisulfate in water, Time= 3h, Ammat., 9 % bient temperature, ohter solvents, other aldehydes and alcohols as substrates, Product distribution Chromat.

Yamazaki, Shigakazu; Yamazaki, Yasuyuki; Chemistry Letters; nb. 4; (1990); p. 571 - 574 View in Reaxys Reaction Steps: 2 1: dihydrogen peroxide; ammonia / water / 1 h / 69.84 °C / |Inert atmosphere; |Autoclave 2: water / water / 7 h / 159.84 °C With ammonia, water, dihydrogen peroxide in water Peng, Hong-Gen; Xu, Le; Wu, Haihong; Zhang, Kun; Wu, Peng; Chemical Communications (Cambridge, United Kingdom); vol. 49; nb. 26; (2013); p. 2709 - 2711,3 View in Reaxys Reaction Steps: 2 1: dihydrogen peroxide; ammonia / water / 8 h / 69.84 - 159.84 °C / |Inert atmosphere; |Autoclave 2: water / water / 7 h / 159.84 °C With ammonia, water, dihydrogen peroxide in water Peng, Hong-Gen; Xu, Le; Wu, Haihong; Zhang, Kun; Wu, Peng; Chemical Communications (Cambridge, United Kingdom); vol. 49; nb. 26; (2013); p. 2709 - 2711,3 View in Reaxys 2H

2H

2H

2

N

2

H

H

O 2

2

H

H

2

H

2

2

H

H

2

H

Rx-ID: 27967161 View in Reaxys 10/35 Yield

Conditions & References With ammonia, iodine in tetrahydrofuran, water, Time= 1h, T= 20 °C Zhao, Hong; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 7; (2008); p. 293 - 296 View in Reaxys

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12/19

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H

N

O

H 2N

O

O

HO

Rx-ID: 35162402 View in Reaxys 11/35 Yield

Conditions & References Reaction Steps: 2 1: dihydrogen peroxide; ammonia / water / 1 h / 69.84 °C / |Inert atmosphere; |Autoclave 2: water / 7 h / 159.84 °C With ammonia, water, dihydrogen peroxide in water Peng, Hong-Gen; Xu, Le; Wu, Haihong; Zhang, Kun; Wu, Peng; Chemical Communications (Cambridge, United Kingdom); vol. 49; nb. 26; (2013); p. 2709 - 2711,3 View in Reaxys Reaction Steps: 2 1: dihydrogen peroxide; ammonia / water / 8 h / 69.84 - 159.84 °C / |Inert atmosphere; |Autoclave 2: water / 7 h / 159.84 °C With ammonia, water, dihydrogen peroxide in water Peng, Hong-Gen; Xu, Le; Wu, Haihong; Zhang, Kun; Wu, Peng; Chemical Communications (Cambridge, United Kingdom); vol. 49; nb. 26; (2013); p. 2709 - 2711,3 View in Reaxys

21 %Chromat., Ca. 15 %Chromat., 40 %Chromat.

With [Ru(η6-C6Me6)Cl2(tris(dimethylamino)phosphine)], hydroxylamine hydrochloride in water, Time= 7h, T= 100 °C , Inert atmosphere, Sealed tube, Green chemistry Garcia-Alvarez, Rocio; Diaz-Alvarez, Alba E.; Crochet, Pascale; Cadierno, Victorio; RSC Advances; vol. 3; nb.

17; (2013); p. 5889 - 5894,6 View in Reaxys

H

N

O

H 2N O

HO

N

Rx-ID: 35258458 View in Reaxys 12/35 Yield

Conditions & References With 4H2O*6K(1+)*PW9V3O40 (6-), ammonia, water, dihydrogen peroxide in isopropyl alcohol, Time= 10h, T= 25 °C Xue, Xiaoling; Song, Fangyuan; Ma, Baochun; Yu, Yongze; Li, Cheng; Ding, Yong; Catalysis Communications; vol. 33; (2013); p. 61 - 65,5 View in Reaxys H

N N

O O

Rx-ID: 31166163 View in Reaxys 13/35 Yield

Conditions & References Reaction Steps: 2 1: acetic acid / water / 0.5 h / 20 °C 2: oxygen; copper(II) bis(trifluoromethanesulfonate) / dimethyl sulfoxide / 0.5 h / 80 °C With oxygen, copper(II) bis(trifluoromethanesulfonate), acetic acid in water, dimethyl sulfoxide Guru, Murali Mohan; Ali, Md Ashif; Punniyamurthy, Tharmalingam; Journal of Organic Chemistry; vol. 76; nb. 13; (2011); p. 5295 - 5308 View in Reaxys

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13/19

2013-06-14 22:30:07

H

N

O

(E)-n-C6H13CH=CHZrCp2Cl Rx-ID: 11963528 View in Reaxys 14/35

Yield

Conditions & References Reaction Steps: 2 1: ethanol / 1 h 2: 97 percent / HOF*CH3CN / 0 °C With HOF* CH3CN in ethanol Carmeli, Mira; Shefer, Neta; Rozen, Shlomo; Tetrahedron Letters; vol. 47; nb. 50; (2006); p. 8969 - 8972 View in Reaxys H O

aminoguanidine salt

N

3-phenyl-1,2-benzisoselenazole Rx-ID: 19933633 View in Reaxys 15/35 Yield

Conditions & References Reaction Steps: 2 1: 82 percent / p-TsOH / CH2Cl2 / 4 h / Heating 2: 67 percent / EtOH / 18 h / Heating With ethanol, toluene-4-sulfonic acid in dichloromethane Neunhoeffer, Hans; Diehl, Werner; Karafiat, Ute; Liebigs Annalen der Chemie; (1989); p. 105 - 110 View in Reaxys Reaction Steps: 2 1: 82 percent / p-TsOH / CH2Cl2 / 5 h / Heating 2: 17 percent / ethanol / Heating With toluene-4-sulfonic acid in ethanol, dichloromethane Neunhoeffer, Hans; Diehl, Werner; Karafiat, Ute; Liebigs Annalen der Chemie; (1989); p. 105 - 110 View in Reaxys Reaction Steps: 3 1: 82 percent / p-TsOH / CH2Cl2 / 5 h / Heating 2: 60 percent / nickelperoxide / CH2Cl2 / 1 h / Ambient temperature 3: 70 percent / MeONa / ethanol / 3 h / Heating With NiO2, sodium methylate, toluene-4-sulfonic acid in ethanol, dichloromethane Neunhoeffer, Hans; Diehl, Werner; Karafiat, Ute; Liebigs Annalen der Chemie; (1989); p. 105 - 110 View in Reaxys H

N H 2N

O

S

Rx-ID: 2690839 View in Reaxys 16/35 Yield

Conditions & References

24 % Chro- With sulfur, ammonia, sodium nitrite, Time= 4h, T= 100 °C mat., 12 % Sato, Ryu; Ityoh, Kaoru; Itoh, Kazumi; Nishina, Hironori; Goto, Takehiko; Saito, Minoru; Chemistry Letters; Chromat.

(1984); p. 1913 - 1916 View in Reaxys

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14/19

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H

N

HI, I2

O

Cp2Zr(isoprene) (1) Rx-ID: 16565856 View in Reaxys 17/35

Yield

Conditions & References Reaction Steps: 2 1: methanol / 0.25 h / 20 °C 2: 97 percent / dimethyl sulphate; K2CO3 / 10 h / Heating With potassium carbonate, dimethyl sulfate in methanol, 1: Addition / 2: Elimination Kamal, Ahmed; Arifuddin, M.; Rao, N. Venugopal; Synthetic Communications; vol. 28; nb. 24; (1998); p. 4507 4512 View in Reaxys H

C-phenyl-C-<2-methoxy-naphthyl-(1)>-methyla‐ mine

O

N

4-isopropyl-phenyl magnesium hal‐ ide Rx-ID: 17251348 View in Reaxys 18/35 Yield

Conditions & References Reaction Steps: 2 1: NH2OH*HCl, AcONa / methanol / 0.5 h / Heating 2: 14 percent Chromat. / CAN / 1 h / 70 °C With ammonium cerium(IV) nitrate, hydroxylamine hydrochloride, sodium acetate in methanol Giurg, M.; Mlochowski, J.; Polish Journal of Chemistry; vol. 71; nb. 8; (1997); p. 1093 - 1101 View in Reaxys H

N H 2N

O

O

N

Rx-ID: 29472286 View in Reaxys 19/35 Yield

Conditions & References With indium(III) nitrate, hydroxylamine hydrochloride, sodium hydrogencarbonate, Time= 20h, T= 100 °C Allen, C. Liana; Burel, Celine; Williams, Jonathan M. J.; Tetrahedron Letters; vol. 51; nb. 20; (2010); p. 2724 - 2726 View in Reaxys

H

O N

N

N N

N

O

O

N

O

N N

NH 2

N H

O

Rx-ID: 2681600 View in Reaxys 20/35 Yield

Conditions & References Time= 2h, T= 180 - 200 °C Badawy, Mohamed A.; Abdel-Hady, Sayed A.; Mahmoud, Ahamed H.; Ibrahim, Yehia A.; Journal of Organic Chemistry; vol. 55; nb. 1; (1990); p. 344 - 347 View in Reaxys

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15/19

2013-06-14 22:30:07

H

O

O

O

N

O

O N

N

N N

N

N

O

N

NH 2

N H

O

Rx-ID: 2681624 View in Reaxys 21/35 Yield

Conditions & References Time= 2h, T= 180 - 200 °C Badawy, Mohamed A.; Abdel-Hady, Sayed A.; Mahmoud, Ahamed H.; Ibrahim, Yehia A.; Journal of Organic Chemistry; vol. 55; nb. 1; (1990); p. 344 - 347 View in Reaxys H

N

O

SASRIN-maleidobenzoic acid resin Rx-ID: 13051133 View in Reaxys 22/35

Yield

Conditions & References Reaction Steps: 2 1: NH2OH*HCl; ZnO / Heating 2: 92 percent / CH3COCl; ZnO / 0.33 h / Heating With hydroxylamine hydrochloride, acetyl chloride, zinc oxide Sarvari, Mona Hosseini; Synthesis; nb. 5; (2005); p. 787 - 790 View in Reaxys H

N

N

N

N

N

O

O

N O

O

Rx-ID: 2678939 View in Reaxys 23/35 Yield

Conditions & References gaseous plasma of glow discharge, Yield given. Further byproducts given. Yields of byproduct given So, Y. H.; Miller, Larry L.; Journal of the American Chemical Society; vol. 103; nb. 14; (1981); p. 4204 - 4209 View in Reaxys H

S HN

N

O S

NH

Rx-ID: 2679402 View in Reaxys 24/35 Yield

Conditions & References in benzene, Heating, Yield given Georg, Gunda I.; Pfeifer, Sarah A.; Tetrahedron Letters; vol. 26; nb. 23; (1985); p. 2739 - 2742 View in Reaxys

NH

HN

H

S

N

S

O

Rx-ID: 2680479 View in Reaxys 25/35 Yield

Conditions & References in benzene, Heating, Yield given Georg, Gunda I.; Pfeifer, Sarah A.; Tetrahedron Letters; vol. 26; nb. 23; (1985); p. 2739 - 2742

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16/19

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View in Reaxys

H

HN

N S

O

S NH

Rx-ID: 2680487 View in Reaxys 26/35 Yield

Conditions & References in benzene, Heating, Yield given Georg, Gunda I.; Pfeifer, Sarah A.; Tetrahedron Letters; vol. 26; nb. 23; (1985); p. 2739 - 2742 View in Reaxys H

N

NH S

O

S

NH

Rx-ID: 2685457 View in Reaxys 27/35 Yield

Conditions & References in benzene, Heating, Yield given Georg, Gunda I.; Pfeifer, Sarah A.; Tetrahedron Letters; vol. 26; nb. 23; (1985); p. 2739 - 2742 View in Reaxys H

N NH

O

S

S

HN

Rx-ID: 2685517 View in Reaxys 28/35 Yield

Conditions & References in benzene, Heating, Yield given Georg, Gunda I.; Pfeifer, Sarah A.; Tetrahedron Letters; vol. 26; nb. 23; (1985); p. 2739 - 2742 View in Reaxys H

N

O

iBu3Al

methylacetylene metal salt

Rx-ID: 14129092 View in Reaxys 29/35 Yield

Conditions & References Reaction Steps: 2 1.1: 0.25 h / 150 - 160 °C 1.2: 78 percent / methanol / 0.5 h / Heating 2.1: PhCHO / 0.5 h / Heating With benzaldehyde Mansour, Abdel Kader; Eid, Mohga M.; Khalil, Nasser S. A. M.; Nucleosides & Nucleotides; vol. 22; nb. 5; (2003); p. 1805 - 1824 View in Reaxys

H

N

O N

N N

N

Rx-ID: 601671 View in Reaxys 30/35 Yield

Conditions & References With hydrogen azide, tin(IV) chloride, benzene

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17/19

2013-06-14 22:30:07

Patent; Knoll and Co.,Schmidt; DE455585; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 2863 View in Reaxys H

N

O

HN O

Rx-ID: 601773 View in Reaxys 31/35 Yield

Conditions & References With hydrogen azide, sulfuric acid, benzene Patent; Knoll and Co., Schmidt; DE427858; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 222 View in Reaxys

O

H

O O

H N

O

H N

N

N

O

N

N NH 2

N

O

O

O

O

Rx-ID: 2687330 View in Reaxys 32/35 Yield

Conditions & References

45 %, 71 % With toluene-4-sulfonic acid in ethanol, Time= 3h, Heating, Product distribution Neunhoeffer, Hans; Diehl, Werner; Karafiat, Ute; Liebigs Annalen der Chemie; (1989); p. 105 - 110 View in Reaxys H

N

HO

H 2N

N

O O

N

O

Rx-ID: 31661981 View in Reaxys 33/35 Yield

Conditions & References Reaction Steps: 2 1: toluene / 72 h / 110 °C 2: 1 h / 700 °C / 0.01 Torr / flash vacuum pyrolysis in toluene Chou, Chin-Hsing; Hsueh, Yu-Tan; Wang, Bo-Chi; Journal of the Chinese Chemical Society (Taipei, Taiwan); vol.

58; nb. 3; (2011); p. 301 - 305 View in Reaxys

H H

NH

H N

O

H

tin vanadate

N

N

Rx-ID: 5957257 View in Reaxys 34/35 Yield

Conditions & References T= 340 - 400 °C Kagarlizkii et al.; ; vol. 32; (1959); p. 388;engl.Ausg.S.404 View in Reaxys

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18/19

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H H

H

O

N H

titanium vanadate

N

NH N

Rx-ID: 5957258 View in Reaxys 35/35 Yield

Conditions & References T= 340 - 400 °C Kagarlizkii et al.; ; vol. 32; (1959); p. 388;engl.Ausg.S.404 View in Reaxys

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19/19

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