反应详情

A suspension of the amide (2) (38 g, 0.1233 mol) in anhydrous acetonitrile (400 ml) was stirred at reflux under nitrogen and t-butyl nitrite (35 ml, 3.17 equiv.) was added quickly. The reflux was continued for 2 hrs. After cooling, the solvent was removed in a rotary evaporator. The residue was taken in water (250 ml) and ethyl acetate (500 ml) and the biphasic mixture was stirred well while solid sodium bicarbonate was slowly added to pH=7.5. Phases were separated and the organic phase was washed with 10% sodium bicarbonate (200 ml). The combined aqueous extracts were washed with ethyl acetate (300 ml), made acidic with 6N hydrochloric acid and extracted with ethyl acetate (2×300 ml). The combined extracts were washed with water (150 ml), dried over sodium sulfate, stripped and the residue was dried in a vacuum oven (50° C.) to produce (3) (24.6 g, 64.7%).

1. temperatureat reflux under nitrogen
2. temperatureAfter cooling
3. customthe solvent was removed in a rotary evaporator
4. stirringethyl acetate (500 ml) and the biphasic mixture was stirred well while solid sodium bicarbonate
5. additionwas slowly added to pH=7.5
6. customPhases were separated
7. washthe organic phase was washed with 10% sodium bicarbonate (200 ml)
8. washThe combined aqueous extracts were washed with ethyl acetate (300 ml)
9. extractionextracted with ethyl acetate (2×300 ml)
10. washThe combined extracts were washed with water (150 ml)
11. dry with materialdried over sodium sulfate
12. customthe residue was dried in a vacuum oven (50° C.)