Benzocaine → HCID 71253061, compound

Participants

Reaction Conditions

Reaction Steps

To 2-chloroethylamine hydrochloride (1.16 g) were added acetonitrile (15 mL) and sulfuryl chloride (6.08 mL), and the mixture was stirred at 80° C. for 8 hr. The solvent was evaporated from the reaction mixture, and to the obtained to residue was added tetrahydrofuran (10 mL). A solution of a mixture of ethyl 4-aminobenzoate (826 mg) and triethylamine (2.8 mL) in tetrahydrofuran (5 mL) was added dropwise under ice-cooling. The reaction mixture was stirred at room temperature overnight, and water was added. The mixture was extracted with ethyl acetate, and the solvent was evaporated. The obtained residue was dissolved in dimethylsulfoxide (15 mL), potassium carbonate (1.38 g) was added, and the mixture was stirred at room temperature. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the solvent was evaporated. The obtained residue was purified by column chromatography (ethyl acetate:hexane) to give the title compound (195 mg).

Provenance & Evidence