Sodium Dithionite → N-(3-aminophenyl)-3-(trifluoromethyl)benzamide

反応式

[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCCC1.O>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=2)[CH:7]=[CH:8][CH:9]=1

参加物

実験手順

To a solution of N-(3-nitrophenyl)-3-(trifluoromethyl)benzamide (30.0 g, 96.7 mmol) in tetrahydrofuran (300 mL) was slowly added with heating under reflux, a solution (500 mL) of sodium hydrosulfite (97.8 g, 562 mmol) in water, and the obtained two-layer solution was vigorously stirred with heating under reflux for 2 days. After cooling the reaction solution to room temperature, the aqueous layer was separated, and extracted with ethyl acetate (150 mL×2). The organic layer separated earlier was diluted with ethyl acetate (350 mL), and washed with saturated aqueous sodium hydrogen carbonate solution (150 mL×2) and saturated brine (100 mL). The combined organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (150 mL×2) and saturated brine (150 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (17.8 g, 66%) as a pale-brown solid.