Benzocaine → Ethyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

Participants

Reaction Steps

A solution of 20.8 g. 14-(trimethylsilyl)tetradecyloxy methanesulfonate and 20 g. ethyl 4-aminobenzoate in 50 ml. hexamethylphosphoramide was stirred at 110° for 18 hr. The reaction was diluted with 100 ml. water and extracted three times with 150 ml. portions of methylene chloride. The combined organic layers were washed with brine, dried with anhydrous magnesium sulfate, passed through a pad of hydrous magnesium silicate, and evaporated. The residue was crystallized from 250 ml. ethanol to yield the title compound as a crystalline solid, m.p. 91°-92° C.

Provenance & Evidence