反応 #414346

反応方程式

water

thionyl chloride

3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid

4-(4-Pyridylsulfonyl)benzenamine

→

propanamide

収率 60.4%

N-[4-(4-Pyridylsulfonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide

収率 60.4%

溶媒

N,N-dimethyl-acetamide

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture stirred at room temperature overnight
2. 2
   ろ過the yellow solid filtered
3. 3
   その他purified by flash chromatography (50% v/v ethyl acetate in methylene chloride)
4. 4
   その他Evaporation of the eluent and trituration of the resulting solid with hot methylene chloride

実験手順

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (4.28 g, 30.5 mmol) in N,N-dimethyl-acetamide (30 mL) was added thionyl chloride (3.63 g, 30.5 mmol) and the mixture stirred at -10° to -15° C. for one hour. 4-(4-Pyridylsulfonyl)benzenamine (4.77 g, 20.4 mmol) was added in one portion and the mixture stirred at room temperature overnight. The solution was poured into water, the yellow solid filtered and purified by flash chromatography (50% v/v ethyl acetate in methylene chloride). Evaporation of the eluent and trituration of the resulting solid with hot methylene chloride yielded the title propanamide (4.61 g, 60%) as an off-white solid; mp 255°-257° C. 1H--NMR (300 MHz, d6 --DMSO): 1.71 (s, 3H, CH3), 7.71 (s, 1H, OH), 8.01 (d, 2H, J=4.5 Hz, aromatic), 8.12 (d, 2H, J=7.1 Hz, aromatic), 8.19 (d, 2H, J=7.1 Hz, aromatic), 9.00 (d, 2H, J=4.5 Hz, aromatic), 10.61 (s, 1H, NH), MS (CI, CH4): 375(M+1).

出典