Triethylamine → HCID 20505010, compound

Participants

Reaction Steps

A mixture of 9.8 g of N-phenylbenzamidine [prepared according to Org. Synth. Coll. IV: 769 (1963)], 8.25 g of the ethyl ester of 4-chloroacetoacetic acid, 100 ml of hexamethyldisilazane, and 7 ml of triethylamine was heated overnight under reflux. The mixture was then diluted with 400 ml of ethyl acetate and washed five times with saturated sodium bicarbonate solution as well as water. After extraction of the aqueous phases with methylene chloride, the combined organic phases were dried and concentrated under vacuum. The residue was purified by column chromatography on silica gel with methylene chloride/0.2-1% isopropanol as well as toluene/40% ethyl acetate as the eluent. Yield: 9.1 g (59%) of the title compound.

Provenance & Evidence