反应详情

A mixture of 4-mercaptobenzoic acid (0.308 g), (R)-N-(2-chloro-4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 197) (0.786 g) and copper (I) oxide (0.143 g) in DMF (5 ml) was stirred and heated under reflux for 1 hour. More 4-mercaptobenzoic acid (0.308 g) was added and heating was continued for a further 2 hours. The mixture was cooled, filtered, and the filter washed with DMF (5 ml). The filtrates were concentrated by evaporation and the residual solid was extracted with boiling ethyl acetate (2×60 ml). The extracts were absorbed onto deactivated silica (silica deactivated by treatment with 10% water) and purified by chromatography eluting with 5% methanol/ethyl acetate to give the title compound (0.803 g) as a solid. NMR: 1.63 (s, 3H), 7.31 (d, 2H), 7.5 (dd, 1H), 7.68 (d, 1H), 7.89 (d, 2H), 8.22 (d, 1H), 9.8 (brs, 1H); MS (ESP−): 418; EA: found: C, 48.2; H, 3.1; N. 3.2%; CH17H13NClF3O4S requires C, 48.6; H, 3.1; N, 3.3%.

1. temperatureheated
2. temperatureunder reflux for 1 hour
3. temperatureheating
4. temperatureThe mixture was cooled
5. filtrationfiltered
6. washthe filter washed with DMF (5 ml)
7. concentrationThe filtrates were concentrated by evaporation
8. extractionthe residual solid was extracted with boiling ethyl acetate (2×60 ml)
9. customThe extracts were absorbed onto deactivated silica (silica deactivated by treatment with 10% water)
10. custompurified by chromatography
11. washeluting with 5% methanol/ethyl acetate