反应详情

Ethyl 4-isothiocyanatothiophene-3-carboxylate (1.1 g) and 4-(2,2,2-trifluoroethoxy)aniline (0.99 g) were dissolved in acetonitrile (40 ml), and the solution was heated under reflux for 1 hr, and allowed to be cooled. Potassium tert-butoxide (1.27 g) was dissolved in ethanol (15 ml), and the solution was poured into the reaction mixture at room temperature. The reaction mixture was heated under reflux for 10 min, allowed to be cooled, and concentrated under reduced pressure. The obtained brown residue was dissolved in ethanol (10 ml), and the solution was poured into 0.3M hydrochloric acid (35 ml) under ice-cooling. The resulting precipitate was collected by filtration, washed with water, and dissolved in tetrahydrofuran (40 ml). The solution was diluted with ethyl acetate (80 ml). This organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a solid. This solid was washed with a mixed solvent of tetrahydrofuran/isopropyl ether (1/10) to give the title compound (1.59 g) as a solid.

1. temperaturethe solution was heated
2. temperatureunder reflux for 1 hr
3. temperatureto be cooled
4. additionthe solution was poured into the reaction mixture at room temperature
5. temperatureThe reaction mixture was heated
6. temperatureunder reflux for 10 min
7. temperatureto be cooled
8. concentrationconcentrated under reduced pressure
9. dissolutionThe obtained brown residue was dissolved in ethanol (10 ml)
10. additionthe solution was poured into 0.3M hydrochloric acid (35 ml) under ice-
11. temperaturecooling
12. filtrationThe resulting precipitate was collected by filtration
13. washwashed with water
14. dissolutiondissolved in tetrahydrofuran (40 ml)
15. additionThe solution was diluted with ethyl acetate (80 ml)
16. dry with materialThis organic layer was dried over anhydrous magnesium sulfate
17. customthe solvent was evaporated under reduced pressure
18. customto give a solid
19. washThis solid was washed with a mixed solvent of tetrahydrofuran/isopropyl ether (1/10)