N,N-Dimethylaniline → HCID 54348876, compound

A solution of 2-hydroxyimino-2-phenylacetonitrile (2.2 g.) and dimethylaniline (1.80 g.) in a mixture of benzene (25 ml.) and dioxane (3 ml.) was added dropwise to a solution of trichloromethyl chloroformate (phosgene dimer) (1.5 g.) in benzene (20 ml.) under ice-cooling. The mixture was stirred for 3 hours at the same temperature and allowed A solution of 1-cyclopropylethanol (1.4 g.) and pyridine (1.2 ml.) in benzene (10 ml.) was added dropwise, under ice-cooling, to the resultant mixture containing 2-chlorocarbonyloxyimino-2-phenylacetonitrile. The mixture was stirred for 2 hours at the same temperature, for 4 hours at room temperature and allowed to stand overnight. The reaction mixture was then washed with 1N hydrochloric acid, water, a sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate. The solvent was distilled off and a small amount of methanol was added to the oily residue. The mixture was allowed to stand in a refrigerator and the precipitated crystals were collected by filtration and recrystallized from methanol to give 2-(1-cyclopropylethoxycarbonyloxyimino)-2-phenylacetonitrile (0.7 g.), mp 65° to 67° C.

1. temperaturecooling
2. additionwas added dropwise, under ice-
3. stirringThe mixture was stirred for 2 hours at the same temperature, for 4 hours at room temperature
4. waitto stand overnight
5. washThe reaction mixture was then washed with 1N hydrochloric acid, water
6. dry with materiala sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate
7. distillationThe solvent was distilled off
8. additiona small amount of methanol was added to the oily residue
9. filtrationthe precipitated crystals were collected by filtration
10. customrecrystallized from methanol

ORD record

ord-4aa3d2fd56414d49af6ce9490c0b38fe

Source dataset

uspto-grants-1978_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04083848