4-Bromophenylhydrazine hydrochloride → 5-Amino-1-(4-bromophenyl)-3-(4-tolyl)pyrazole-4-carboxamide

반응식

[C:1]([C:3](=[C:7](SC)[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:4]([NH2:6])=[O:5])#[N:2].Cl.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][NH2:26])=[CH:21][CH:20]=1.[OH-].[Na+]>>[NH2:2][C:1]1[N:25]([C:22]2[CH:23]=[CH:24][C:19]([Br:18])=[CH:20][CH:21]=2)[N:26]=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

참가 물질

반응물 3

HCID 121574-Bromophenylhydrazine hydrochloride

HCID 14798Sodium Hydroxide

HCID 542422372-Cyano-3-methylthio-3-(4-tolyl)acrylamide2회

생성물 1

HCID 538502285-Amino-1-(4-bromophenyl)-3-(4-tolyl)pyrazole-4-carboxamide수율 31.7%

실험 절차

The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl)acrylamide (928 mg, 4.0 mmol), 4-bromophenylhydrazine hydrochloride (894 mg, 4.0 mmol) and sodium hydroxide (176 mg, 4.4 mmol) following the procedure used for the compound of Example 12. The crude product was subjected to column chromatography (SiO2, 10% methanol in CH2Cl2) and recrystallisation from ethyl acetate to give the title compound as white crystals (470 mg) m.p. 222-223°. δH (CDCl3) 7.63 (2H, dt, J 8.8, 2.2 Hz), 7.52 (2H, dt, J 8.5, 2.6 Hz), 7.48 (2H, d, J 7.4 Hz), 7.28 (2H, d, J 8.3 Hz), 5.74 (2H, br s), 5.29 (2H, br s), 2.41 (3H, s).