N,N-Dimethylaniline → HCID 85862764, compound

Participants

Reaction Steps

A solution of benzophenone oxime (9.85 g.) and dimethylaniline (6.6 g.) in a mixture of benzene (50 ml.) and dioxane (10 ml.) was dropwise added to a solution of trichloromethyl chloroformate (phosgene dimer) (5.5 g.) in benzene (15 ml.) under ice-cooling, and the mixture was stirred for 1 hour at the same temperature, for 2 hours at room temperature and allowed to stand overnight. To the resultant mixture containing benzophenone O-chlorocarbonyloxime was dropwise added a solution of tert-butyl alcohol (5.6 g.) and pyridine (6.0 ml.) in benzene (20 ml.) under ice-cooling, and the mixture was stirred for 6 hours at the same temperature and allowed to stand overnight. 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 solvent was distilled off and to the resulting crystals was added petroleum ether. The crystals were collected by filtration and dried to give benzophenone O-tert-butoxycarbonyloxime (10.5 g.), mp 126° to 133° C. A small amount of the crystals was recrystallized from a mixture of toluene and petroleum ether to give pure compound, mp 131° to 133° C.

Provenance & Evidence