反应详情

A solution of dimethylaniline (6.0 ml.) in benzene (15 ml.) was dropwise added to a suspension of 2-hydroxyimino-2-phenylacetonitrile (7.3 g.) and phosgene (5.0 g.) in benzene (50 ml.) over 40 minutes under ice-cooling. The mixture was stirred for 2 hours at the same temperature and allowed to stand overnight. To the mixture containing 2-chlorocarbonyloxyimino-2-phenylacetonitrile was dropwise added a solution of 4-methoxybenzyl alcohol (6.9 g.) and pyridine (4.0 ml.) in benzene (20 ml.) over 30 minutes under ice-cooling, and the mixture was stirred for 7 hours at room temperature. The reaction mixture was in turn washed with water, 1N hydrochloric acid, water, a sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate. The solution was concentrated, and the residual crystals were triturated in n-hexane and collected by filtration. The crystals were recrystallized from a mixture of ethyl acetate and n-hexane to give 2-(4-methoxybenzyl)oxycarbonyloxyimino-2-phenylacetonitrile (3.1 g.). Mp 112° to 113° C. The mother liquor was concentrated to give the object compound (2.4 g.). Total yield (5.5 g.).

1. temperaturecooling
2. waitto stand overnight
3. temperaturecooling
4. stirringthe mixture was stirred for 7 hours at room temperature
5. washwashed with water, 1N hydrochloric acid, water
6. dry with materiala sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate
7. concentrationThe solution was concentrated
8. customthe residual crystals were triturated in n-hexane
9. filtrationcollected by filtration
10. customThe crystals were recrystallized from a mixture of ethyl acetate and n-hexane