反应详情

A mixture of 4-(2-methyl-1-(1H)-imidazolyl)-1-(4-trifluoromethylphenyl)-1-butanone (2.65 g), O-(2-aminoethyl)hydroxylamine dihydrochloride (1.60 g), 3 equivalents of pyridine, and absolute ethanol (75 nil) was heated under reflux, under nitrogen, with stirring, for three hrs. The reaction mixture was diluted with 10% sodium hydroxide solution and ethyl acetate. The layers were separated. The aqueous phase was extracted with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated. The residue was taken up in toluene and 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 from absolute ethanol/ether to give 1.4 g (37%) of product, mp 181°-184° C. (dec).

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