反応 #414350

反応方程式

water

thionyl chloride

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

4-(2-Thienylsulfonyl)benzenamine

→

propanamide

収率 77.0%

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

収率 77.0%

溶媒

N,N-dimethylacetamide

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture stirred at room temperature overnight
2. 2
   抽出the aqueous solution extracted with ethyl acetate (2×50 mL)
3. 3
   乾燥dried (MgSO4)
4. 4
   ろ過filtered
5. 5
   workup.DISTILLATIONthe solvent distilled
6. 6
   その他to yield a tan solid
7. 7
   洗浄Flash chromatography of the solid (eluted with 5% v/v ethyl acetate in methylene chloride) and
8. 8
   その他evaporation of the eluent

実験手順

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (0.50 g, 3.1 mmol) in N,N-dimethylacetamide (7 mL) was added thionyl chloride (0.37 g, 3.1 mmol) and the mixture stirred at -10° to -15° C. for 1 hour. 4-(2-Thienylsulfonyl)benzenamine (0.50 g, 2.1 mmol) was added in one portion to the orange solution and the mixture stirred at room temperature overnight. The brown solution was poured into water and the aqueous solution extracted with ethyl acetate (2×50 mL). The organics were combined, dried (MgSO4), filtered and the solvent distilled to yield a tan solid. Flash chromatography of the solid (eluted with 5% v/v ethyl acetate in methylene chloride) and evaporation of the eluent yielded the title propanamide (0.61 g, 77%) as an off-white solid; mp 158°-161 0C. 1H--NMR (250 MHz, d6 --DMSO): 1.57 (s, 3H, CH3), 7.21 (dd, 1H, J=4.9, 4.0 Hz, aromatic), 7.56 (s, 1H, OH), 7.81 (dd, 1H, J=3.8, 1.5 Hz, aromatic), 8.00 (m, 5H, aromatic), 10.43 (s, 1H, NH). MS (CI, CH4): 380(M+1).

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