Triethylamine → Methyl 4-[[[3-chloro-5-methoxybenzo[b]thien-2yl]carbonyl]amino]benzoate

Participants

Reaction Steps

To a 0° C. solution of 3-chloro-5-methoxybenzo[b]thiophene-2-carbonyl chloride (500 mg, 1.9 mmol) in 20 mL of THF is added methyl p-aminobenzoate (318 mg, 2.1 mmol) followed by triethylamine (293 μL, 2.1 mmol). The reaction mixture is allowed to warm to room temperature and stirring is continued overnight. The mixture is partitioned between ethyl acetate and 1N HCl, then washed with 1N NaOH, saturated NaHCO3, and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate:hexane provides 225 mg of methyl 4-[[[3-chloro-5-methoxybenzo[b]thien-2yl]carbonyl]amino]benzoate; mp=205°-206° C.

Provenance & Evidence