反应详情

温度

35 °C

Tetrahydrofuran (5ml,dry) was added to a mixture of 2,2-bis-trifluoromethyl-2-hydroxyacetic acid (1.29 g, 6.1 mmol) and 1,1'-carbonyldiimidazole (0.99 g, 6.1 mmol), while under a nitrogen atmosphere. There was an immediate evolution of carbon dioxide. The reaction was heated at 35° C. for 15 min. The reaction was treated with a solution of 4-(4-pyridylsulfonyl)benzeneamine (1.43 g, 6.1 mmol) in dimethylformamide (15 ml, dry), and heated to 69° C. in an ultrasonic bath for 19.5 hrs. The reaction was poured into water (300 ml), and extracted with ethyl ether (3×300 ml). The combined organic portions were evaporated and preabsorbed onto silica gel (10 gm). Chromatography of this material on silica gel, eluting with methylene chloride/ethyl acetate (first 100:0 and then 70:30) provided a white solid. Recrystallization from acetone gave starting 4-(4-pyridylsulfonyl)benzeneamine. The filtrate was evaporated and chromatographed on silca gel eluting with chloroform/methanol (first 100:0 and then 98:2) provided the title compound (0.115 g, 6%) as a white solid; mp 235°-237° C. 1H--NMR (250 MHz, d6 --DMSO): 7.90 (d, J=4.6, 2H, ArH), 8.04 (d, 4H, ArH), 8.89 (d, J=4.68Hz, 2H, ArH), 9.90 (s, 1H, OH), 10.97 (s, 1H, NH). MS(CI,CH4): 429 (M+1).

1. temperatureheated to 69° C. in an ultrasonic bath for 19.5 hrs
2. extractionextracted with ethyl ether (3×300 ml)
3. customThe combined organic portions were evaporated
4. custompreabsorbed onto silica gel (10 gm)
5. washChromatography of this material on silica gel, eluting with methylene chloride/ethyl acetate (first 100:0
6. custom70:30) provided a white solid
7. customRecrystallization from acetone
8. customgave
9. customThe filtrate was evaporated
10. customchromatographed on silca gel
11. washeluting with chloroform/methanol (first 100:0