反应详情

A mixture of 1-(4-chlorophenyl)-4-(1-(1H)-imidazolyl)-1-butanone (2.20 g), O-(2-aminoethyl)hydroxylamine dihydrochloride (1.58 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 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 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 twice from absolute ethanol/ether to give 1.3 g (39%) of product, mp 205°-207° C. (dec).

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