反应详情

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 (1.00 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, CH3), 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).

1. stirringthe mixture stirred at room temperature overnight
2. extractionextracted with ethyl acetate (2×50 mL)
3. washThe combined organic portions were washed with water
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. distillationthe solvent distilled
7. customto yield a tan solid
8. washFlash chromatography of the solid (eluted with 10% v/v ethyl acetate in methylene chloride) and
9. customevaporation of the eluent