N,N-Dimethylaniline → 2-(4-Methoxybenzyloxycarbonyloxyimino)-2-phenylacetonitrile

A solution of dimethylaniline (6.0 ml.) in benzene (15 ml.) was added dropwise to a suspension of 2-hydroxyimino-2-phenylacetonitrile (7.3 g.) and phosgene (5.0 g.) in benzene (50 ml.) for 40 minutes under ice-cooling. The mixture was stirred for 2 hours at the same temperature and allowed to stand overnight. A solution of 4-methoxybenzyl alcohol (6.9 g.) and pyridine (4.0 ml.) in benzene (20 ml.) was added dropwise, for 30 minutes under ice-cooling to the mixture containing 2-chlorocarbonyloxyimino-2-phenylacetonitrile. The mixture was stirred for 7 hours at room temperature. The reaction mixture was then 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 desired compound (2.4 g.). Total yield (5.5 g.).

1. temperaturecooling
2. waitto stand overnight
3. temperaturecooling to the mixture
4. stirringThe mixture was stirred for 7 hours at room temperature
5. washThe reaction mixture was then washed 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

ORD record

ord-5a276a56c8254b44ae828871b9d433ce

Source dataset

uspto-grants-1977_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04014915