Acetic Acid → HCID 178488268, compound

Participants

Reaction Steps

A mixture of 5.7 g (0.023 mole) of 5-methoxy-3-(1-methylethoxy)-2-benzofurancarboxylic acid and 4.2 g (0.026 mole ) of 1,1-carbonylbis(1H-imidazole) in 140 ml of acetonitrile is stirred at reflux for one hour. The mixture is cooled, treated with 2.3 g (0.027 mole) of anhydrous 5-aminotetrazole plus 7.7 ml (5.6 g; 0.055 mole) of triethylamine, and heated at reflux for an additional five hours. The cooled reaction mixture is added to 1.5 kg of ice/water and acidified with glacial acetic acid to precipitate the tetrazole product. The precipitate is filtered, washed with water, and recrystallized from aqueous acetonitrile to yield 6.0 g (82% yield) of the analytically pure 5-methoxy3-tetrazol-5-yl-2-benzofurancarboxamide, mp 241°-245° C.

Provenance & Evidence