2,5-Dimethyl-4-phenyl-1H-imidazole [C11H12N2]

2,5-Dimethyl-4-phenyl-1H-imidazole [C11H12N2]

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1. Query

N

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Date

10 reactions in Reaxys

2018-07-20 14h:42m:12s (UTC)

HN

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='13739-49-6') AND (IDE.INCHI='LHKCCUVBNACJKHUHFFFAOYSA-N') NOT (RX.RXRN=5040))

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2018-07-20 14:43:31

2,5-Dimethyl-4-phenyl-1H-imidazole [C11H12N2]

HN

NH 2

O

O N

N

HN

O

Rx-ID: 40558977 View in Reaxys 1/10 Yield 90 %

Conditions & References Stage 1: With sodium methylate in methanol, Time= 0.5h, T= 25 °C , Green chemistry Stage 2: in methanol, Time= 8h, T= 25 °C , Green chemistry Guo, Xiao; Shao, Jiaan; Liu, Huan; Chen, Binhui; Chen, Wenteng; Yu, Yongping; RSC Advances; vol. 5; nb. 64; (2015); p.

51559 - 51562 View in Reaxys

O HN

N

NH 2

O

Cl

N

H

HN

Rx-ID: 35955445 View in Reaxys 2/10 Yield 55 %

Conditions & References Typical procedure for the synthesis of 5-Methyl-2,4-diphenyl-1H-imidazole General procedure: In an oven dried 10 mL round bottom flask, benzamidinehydrochloride (78 mg, 0.5 mmol), (2-nitro-propenyl)-benzene (81 mg,0.5 mmol), nano In2O3 (7 mg, 5 mol percent), K2CO3 (69 mg, 1 equiv), and dry EtOH(2 mL) were added and stirred for 6 h at 70 C. The progress of the reaction wasmonitored by TLC. After completion of the reaction the excess EtOH wasevaporated in a rotary evaporator and the crude reaction mixture was dilutedwith water (3 mL), and extracted with DCM. The organic layer was dried overanhydrous Na2SO4 and evaporated under vacuum. The residue was purified bycolumn chromatography (hexane/ethyl acetate as eluent) to afford theanalytically pure product With indium(III) oxide, potassium carbonate in ethanol, Time= 6h, T= 70 °C , Green chemistry Mitra, Shubhanjan; Bagdi, Avik Kumar; Majee, Adinath; Hajra, Alakananda; Tetrahedron Letters; vol. 54; nb. 36; (2013); p. 4982 - 4985 View in Reaxys

HN

NH 2

O

N

S O

O

HN

O

Rx-ID: 8892740 View in Reaxys 3/10 Yield

Conditions & References in chloroform, acetonitrile, Time= 3.5h, Heating Zhang; Chen; Synthesis; nb. 14; (2001); p. 2075 - 2077 View in Reaxys

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2018-07-20 14:43:31

2,5-Dimethyl-4-phenyl-1H-imidazole [C11H12N2]

O N

HN

Rx-ID: 15138465 View in Reaxys 4/10 Yield

Conditions & References Reaction Steps: 2 1: acetonitrile / 0.75 h / Heating 2: acetonitrile; CHCl3 / 3.5 h / Heating in chloroform, acetonitrile Zhang; Chen; Synthesis; nb. 14; (2001); p. 2075 - 2077 View in Reaxys

N

HN

Rx-ID: 5678176 View in Reaxys 5/10 Yield

Conditions & References Propiophenon, 1) Br2 (equimol. Mengen)(75grad), 2) Acetamid, NH3 (Durchleiten v. NH3) (160-160.5, 5h; Ausb.59percent) Marquez; Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica; vol. 57; (1961); p. 723,729 View in Reaxys Essigsaeure-(1-oxo-1-phenyl-prop-2-ylester)(A23), Ammoniumacetat, sd. Eg. (in sehr geringen Mengen) Strzybny et al.; Journal of the South African Chemical Institute; vol. 22; (1969); p. 158,160,162 View in Reaxys 1b, Acetimidsaureathylester Gnichtel,H. et al.; Chemische Berichte; vol. 105; (1972); p. 1865 - 1874 View in Reaxys PhCOCHMeOAc, (NH4)2CO3 Novelli; de Santis; Boletin de la Sociedad Quimica del Peru; vol. 33; (1967); p. 111,112-117; ; vol. 69; nb. 36032a; (1968) View in Reaxys AcCHPhOAc, (NH4)2CO3 Novelli; de Santis; Boletin de la Sociedad Quimica del Peru; vol. 33; (1967); p. 111,112-117; ; vol. 69; nb. 36032a; (1968) View in Reaxys N-Oxid (VIII), PCl3 Volodarsky et al.; Tetrahedron Letters; (1965); p. 1565 View in Reaxys 2,4-Dimethyl-5-phenyl-imidazol-3-oxid, PCl3 Volodarsky et al.; Tetrahedron Letters; (1965); p. 1565 View in Reaxys 2,5-Dimethyl-4-phenyl-imidazol-3-oxid, PCl3/CHCl3 Volodarsky et al.; Tetrahedron Letters; (1965); p. 1565 View in Reaxys

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2018-07-20 14:43:31

2,5-Dimethyl-4-phenyl-1H-imidazole [C11H12N2]

Essigsaeure-(1-benzoylethyl)-ester, Formamid (ueb. 2,5-Dimethyl-4-phenyloxazol) Novelli; De Santis; Tetrahedron letters; vol. 3; (1967); p. 265 - 269 View in Reaxys (yield)85percent Novelli; De Santis; Tetrahedron letters; vol. 3; (1967); p. 265 - 269 View in Reaxys

N

N

N

HN

N

HN

N H

N

Rx-ID: 141374 View in Reaxys 6/10 Yield

Conditions & References With ethanol, acetic acid, zinc Metze; Scherowsky; Chemische Berichte; vol. 92; (1959); p. 2481,2485 View in Reaxys

O

OH

OH

N

zinc

N N

N

N

HN

HN

N H

Rx-ID: 5678178 View in Reaxys 7/10 Yield

Conditions & References Metze; Scherowsky; Chemische Berichte; vol. 92; (1959); p. 2481,2485 View in Reaxys

N

N

N

3,6-dimethyl-5-phenyl-1,2(?)-dihydro-<1,2,4>triazine

HN N

Rx-ID: 5678179 View in Reaxys 8/10 Yield

Conditions & References With ethanol, acetic acid, zinc Metze; Scherowsky; Chemische Berichte; vol. 92; (1959); p. 2481,2485 View in Reaxys

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2018-07-20 14:43:31

2,5-Dimethyl-4-phenyl-1H-imidazole [C11H12N2]

O

O N O

HN

Rx-ID: 637243 View in Reaxys 9/10 Yield

Conditions & References With ammonium hydroxide Carrara et al.; Chimica e l'Industria (Milan, Italy); vol. 28; (1946); p. 9 View in Reaxys

O N

<NH4>2CO3 N

HN O

Rx-ID: 5678177 View in Reaxys 10/10 Yield

Conditions & References With ethanol Craig; Henze; Journal of Organic Chemistry; vol. 10; (1945); p. 10,13 View in Reaxys

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5/5

2018-07-20 14:43:31