反应详情

Under a nitrogen atmosphere a solution of 3.0 grams (8.2 mmole) of 3-(4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione, and 20 mL of acetic acid in 80 mL of ethanol was stirred, and 1.8 grams (32 mmole) of iron powder was added. The reaction mixture was then heated under reflux for one hour, after which analysis by thin layer chromatography (TLC) indicated that the reaction was complete. The reaction mixture was concentrated under reduced pressure. The concentrate was then taken up in 50 mL of aqueous 5% sodium bicarbonate solution and 100 mL of ethyl acetate. The mixture was filtered through diatomaceous earth, and the filter cake was washed with 20 mL of water and three 50 mL portions of ethyl acetate. The filtrate was placed in a separatory funnel and 100 mL of aqueous 5% sodium bicarbonate solution was added. The aqueous phase was separated and the organic phase was washed with 50 mL of aqueous saturated sodium bicarbonate solution, then with 50 mL of aqueous saturated sodium chloride solution. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 2.6 grams of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)pyrimidinedione. The NMR spectrum was consistent with the proposed structure.

1. temperatureThe reaction mixture was then heated
2. temperatureunder reflux for one hour
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. filtrationThe mixture was filtered through diatomaceous earth
5. washthe filter cake was washed with 20 mL of water and three 50 mL portions of ethyl acetate
6. customThe filtrate was placed in a separatory funnel
7. addition100 mL of aqueous 5% sodium bicarbonate solution was added
8. customThe aqueous phase was separated
9. washthe organic phase was washed with 50 mL of aqueous saturated sodium bicarbonate solution
10. dry with materialThe organic layer was dried with magnesium sulfate
11. filtrationfiltered
12. concentrationThe filtrate was concentrated under reduced pressure