反应详情

To a solution of 1-isothiocyanato-4-(2,2,2-trifluoroethoxy)benzene (1.77 g) in N,N-dimethylformamide (25 mL) was added sodium hydride (60% in oil, 0.478 g) under ice-cooling. The reaction mixture was stirred for 5 min under ice-cooling, diethyl 2-carbamimidoylpentane-1,5-dioate (2.5 g) was added thereto, and the mixture was stirred for 30 min under ice-cooling. To the reaction mixture was added 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in ethanol (25 mL), sodium ethoxide (20% ethanol solution, 10.6 mL) was added thereto, and the mixture was stirred for 30 min. To the reaction mixture was added 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.75 g).

1. temperaturecooling
2. temperaturecooling
3. stirringthe mixture was stirred for 30 min under ice-
4. temperaturecooling
5. extractionthe mixture was extracted with ethyl acetate
6. washThe extract was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. customThe solvent was evaporated under reduced pressure
9. dissolutionThe residue was dissolved in ethanol (25 mL)
10. additionsodium ethoxide (20% ethanol solution, 10.6 mL) was added
11. stirringthe mixture was stirred for 30 min
12. additionTo the reaction mixture was added 1M hydrochloric acid
13. extractionthe mixture was extracted with ethyl acetate
14. washThe extract was washed with saturated brine
15. dry with materialdried over anhydrous sodium sulfate
16. customThe solvent was evaporated under reduced pressure
17. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)