Benzocaine → Ethyl 4-[2-benzyloxy-5-bromophenylacetamido]benzoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-benzyloxy-5-bromophenylacetic acid (3.2 g) in toluene (100 ml) was added thionyl chloride (1.0 ml) and DMF (3 drops). The reaction was stirred at 80° C. for 1 hour and cooled to ambient temperature ethyl 4-aminobenzoate (2.0 g) and triethylamine (2 ml) were added to the reaction mixture with stirring. After standing for 18 hours, the mixture was diluted with dichloromethane and washed with water, 1N HCl solution, water and sautrated aqueous NaHCO3 solution. The organic extract was dried (MgSO4), filtered and evaporated and the residue purified by trituration with diethyl ether to give ethyl 4-[2-benzyloxy-5-bromophenylacetamido]benzoate (2.0 g) mpt. 174-176° C.

Provenance & Evidence