反应详情

The oil of a 4.0 g (100 mmol) portion of 60 percent in mineral oil sodium hydride was removed by triple extraction with hexane and was replaced with 100 mL of tetrahydrofuran. 4-Chloroacetophenone (4.33 g, 28 mmol) was added and the mixture was heated at reflux with stirring for 1 hr and then allowed to cool. 5-Methylsulfonyl-3-(trifluoromethyl)isothiazole (4.57 g, 19.8 mmol) dissolved in a small amount of tetrahydrofuran was added and the mixture was heated at reflux with stirring for 3 hr and then allowed to cool. The mixture was next acidified with 60 mL of 10 percent aqueous acetic acid and the layers that formed were separated. The aqueous layer was extracted with 2×100 mL of ether and the organic fractions were combined, washed with aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a residue. This residue was washed with hexane and crystallized from a 1:1 mixture of dichloromethane and hexane to obtain 3.19 g (53 percent of theory) of the title compound as a solid melting at 109°-110° C.

1. customThe oil of a 4.0 g (100 mmol) portion of 60 percent in mineral oil sodium hydride was removed by triple extraction with hexane
2. temperaturethe mixture was heated
3. temperatureat reflux
4. temperatureto cool
5. additionwas added
6. temperaturethe mixture was heated
7. temperatureat reflux
8. stirringwith stirring for 3 hr
9. temperatureto cool
10. customthe layers that formed
11. customwere separated
12. extractionThe aqueous layer was extracted with 2×100 mL of ether
13. washwashed with aqueous sodium bicarbonate solution
14. dry with materialdried over sodium sulfate
15. filtrationfiltered
16. concentrationconcentrated by evaporation under reduced pressure
17. customto obtain a residue
18. washThis residue was washed with hexane
19. customcrystallized from a 1:1 mixture of dichloromethane and hexane