Benzocaine → HCID 69316798, compound

Participants

Reaction Steps

To a flask containing thionyl chloride (1.52 g, 929 μl, 12.8 mmol) and 1 drop of DMF is added cyclohexylphenylacetic acid (1.87 g, 8.54 mmol). The resulting solution is stirred for 1 h. The thionyl chloride is evaporated under reduced pressure and the resulting crude acid chloride is diluted in dichloromethane (15 ml). To this solution is added dropwise a solution of 4-amino-benzoic acid ethyl ester (1.41 g, 8.54 mmol) and triethylamine (1.49 ml, 1.08 g, 10.67 mmol) in dichloromethane (15 ml). The resulting mixture is stirred for 30 min at rt. It is diluted with dichloromethane and the resulting organic phase is washed with a 10% aqueous citric acid solution, with a saturated aqueous Na2CO3 solution and with water. It is dried over Na2SO4 and the solvent is evaporated in vacuo. The crude residue is purified on silica gel (AcOEt/heptane, 1.4), yielding the title compound (3.04 g) in 97% as a white solid: tR=8.00 min (LC-1), ESI-MS (pos.): m/z 366.18 [M+H]+, ESI-MS (neg.): m/z 364.25 [M−H]+.

Provenance & Evidence