Benzophenone imine → Ethyl 2-(diphenylmethyleneamino)acetate

Participants

Reaction Steps

Benzophenone imine (100 g, 0.54 mol), and 78.4 g, 0.56 mol) ethyl glycinate hydrochloride are combined in 2 L of dichloromethane and stirred overnight at room temperature. A precipitate (ammonium chloride) is filtered and the solution washed with water, dried over magnesium sulfate, and concentrated. The residual oil is dissolved in 200 mL of boiling diethyl ether, cooled to room temperature, and diluted with 600 mL of hexane. Some seed crystals from a previous experiment are added and the mixture cooled at +2° C. overnight. A white crystalline precipitate is collected and the mother liquor is concentrated to one-half of the volume, cooled overnight as above. This affords a second crop of product. The total yield is 133.0 g of the title compound; mp 52°-54° C.

Provenance & Evidence