反応 #414347

反応方程式

water

thionyl chloride

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

4-(2-Pyrimidylsulfonyl)benzenamine

→

propanamide

収率 66.6%

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

収率 66.6%

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extracted with ethyl acetate (2×50 mL)
3. 3
   洗浄The combined organic portions were washed with water
4. 4
   乾燥dried (MgSO4)
5. 5
   ろ過filtered
6. 6
   workup.DISTILLATIONthe solvent distilled
7. 7
   その他to yield a tan solid
8. 8
   洗浄Flash chromatography of the solid (eluted with 10% v/v ethyl acetate in methylene chloride) and
9. 9
   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 (1.01 g, 6.4 mmol) in N,N-dimethylacetamide (10 mL) was added thionyl chloride (0.76 g, 6.4 mmol) and the mixture stirred at -10° to -15° C. for one hour. 4-(2-Pyrimidylsulfonyl)benzenamine (100 g, 4.2 mmol) was added in one portion to the orange solution and the mixture stirred at room temperature overnight. The brown mixture was poured into water and extracted with ethyl acetate (2×50 mL). The combined organic portions were washed with water, dried (MgSO4), filtered, and the solvent distilled to yield a tan solid. Flash chromatography of the solid (eluted with 10% v/v ethyl acetate in methylene chloride) and evaporation of the eluent yielded the title propanamide (1.05 g, 66%) as a white solid; mp 187°-190° C. 1H--NMR (300 MHz, d6 --DMSO): 1.60 (s, 3H, CH 3), 7.59 (s, 1H, OH), 7.79 (t, 1H, J=4.9 Hz, aromatic), 7.96 (d, 2H, J=8.9 Hz, aromatic), 8.06 (d, 2H, J=8.9 Hz, aromatic), 9.02 (d, 2H, J=4.8 Hz, aromatic), 10.49 (s, 1H, NH). MS (CI, CH4): 376 (M+1).

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