Dimethyl Sulfoxide → [3-(2-Quinolinylmethyloxy)benzyloxy]-3-methylbenzo(b)thiophene-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-methyl-5-[3-(2-quinolinylmethyloxy)benzyloxy]benzo(b)thiophene-2-carboxylic acid (250 mg, 0.55 mmol) in DMSO (6 ml) at room temperature is added 1,1'-carboxyldiimidazole (178 mg, 1.10 mmol) and the resulting solution is stirred at 60° C. for 1 hour. Triethylamine (153 μL, 1.10 mmol) and 5-aminotetrazole monohydrate (113.2 mg, 1.10 mmol) are added successively and the solution stirred at 60° C. for 16 hours. The reaction mixture is cooled to room temperature and poured over ice-water. The pH is adjusted to 10 and the aqueous layer washed with ether. The pH is then adjusted to 3 and the precipitated material obtained by filtration and washing successively with water, ethanol and methylene chloride. Further drying under vacuum affords N-1H-(5-tetrazolyl)-5-[3-(2-quinolinylmethyloxy)benzyloxy ]-3-methylbenzo(b)thiophene-2-carboxamide (M.P. 220-224° C. (dec)).

Provenance & Evidence