反应详情

A mixture of 4-(1-(1H)-imidazolyl)-1-(4-trifluoromethylphenyl)-1-butanone (5.00 g), O-(2-aminoethyl)hydroxylamine dihydrochloride (3.17 g), 3 equivalents of pyridine, and absolute ethanol (75 ml) was heated under reflux, under nitrogen, with stirring, for two hrs. The reaction mixture was evaporated, toluene was added and evaporated. The residue was partitioned between 10% sodium hydroxide solution and ethyl acetate. The layers were separated and the aqueous phase extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated. The residue was purified by flash chromatography (180: 19:1 dichloromethane/methanol/ammonium hydroxide). The appropriate fractions were collected and concentrated. The residue was dissolved in absolute ethanol and treated with ethereal hydrogen chloride. Diethyl ether was added. The precipitate was collected and recrystallized twice from absolute ethanol/ether to give 3.1 g (42%) of product, mp 207°-208C. (dec).

1. temperaturewas heated
2. temperatureunder reflux, under nitrogen
3. customThe reaction mixture was evaporated
4. additiontoluene was added
5. customevaporated
6. customThe residue was partitioned between 10% sodium hydroxide solution and ethyl acetate
7. customThe layers were separated
8. extractionthe aqueous phase extracted with ethyl acetate
9. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
10. filtrationfiltered
11. customthe filtrate was evaporated
12. customThe residue was purified by flash chromatography (180: 19:1 dichloromethane/methanol/ammonium hydroxide)
13. customThe appropriate fractions were collected
14. concentrationconcentrated
15. dissolutionThe residue was dissolved in absolute ethanol
16. additiontreated with ethereal hydrogen chloride
17. additionDiethyl ether was added
18. customThe precipitate was collected
19. customrecrystallized twice from absolute ethanol/ether