Benzocaine → N,N-Diphenyl-N'-(4-ethoxycarbonylphenyl)formamidine

Participants

Reaction Steps

To a solution of N,N-diphenylformamide (19.7 g, 0.10 mol) in 100 ml of chloroform was added 22.8 g (0.11 mol) of phosphorus pentachloride in small portions. After the addition was completed the solution was refluxed for 1 hr. Ethyl 4-aminobenzoate (16.5 g, 0.10 mol) was added in small portions and the solution was refluxed 1 hr. The solution was poured into 100 ml of water and neutralized with concentrated ammonium hydroxide. The chloroform phase was separated, dried (MgSO4), filtered and concentrated to yield a yellow oil. Purification by chromatography using silica gel/benzene yielded the desired product. ##STR11##

Provenance & Evidence