反应详情

温度

100 °C

4-(p-Chlorophenyl)semicarbazide (1.49 g, 8.03 mmol) is added to a solution of 2-(trifluoromethyl)-4H-3,1-benzoxazin-4-one (1.72 g, 8.00 mmol) in pyridine (27 mL) at 100° C. The reaction mixture is stirred for 15 hours at 100° C., cooled to room temperature and concentrated in vacuo to obtain a solid. The solid is diluted with dichloromethane and the mixture is washed sequentially with 10% hydrochloric acid and water and concentrated in vacuo to obtain a tan solid. The tan solid is washed with dichloromethane and filtered. The filtrate is concentrated in vacuo to obtain a brown foam. The foam is diluted with ether and the mixture is washed sequentially with 10% hydrochloric acid, water and saturated sodium hydrogen carbonate solution, dried over anhydrous MgSO4, decolorized with carbon and concentrated in vacuo to obtain a cream colored foam. Flash chromatography of the cream colored foam using silica gel and a 3:1 dichloromethane/hexanes solution gives the title product as a white solid, 0.36 g, which is identified by 1HNMR spectral analysis.

1. temperaturecooled to room temperature
2. concentrationconcentrated in vacuo
3. customto obtain a solid
4. washthe mixture is washed sequentially with 10% hydrochloric acid and water
5. concentrationconcentrated in vacuo
6. customto obtain a tan solid
7. washThe tan solid is washed with dichloromethane
8. filtrationfiltered
9. concentrationThe filtrate is concentrated in vacuo
10. customto obtain a brown foam
11. washthe mixture is washed sequentially with 10% hydrochloric acid, water and saturated sodium hydrogen carbonate solution
12. dry with materialdried over anhydrous MgSO4
13. concentrationconcentrated in vacuo
14. customto obtain a cream colored foam