Hydrochloric Acid → HCID 178522682, compound

Participants

Reaction Conditions

Reaction Steps

Dry 2-benzyloxy-5-chlorobenzoic acid (1.15 g) was treated, with stirring, with dry pyridine (20 ml) and anhydrous 5-aminotetrazole (3.72 g). The mixture was stirred at 25° C. and treated dropwise with silicon tetrachloride (0.45 g), and the mixture was then stirred at 25° C. for 20 hours. The resulting clear yellow solution was cautiously poured into a mixture of ice and water (50 ml) and the mixture was acidified to pH 1 by treatment with concentrated hydrochloric acid. The white precipitated solid was filtered off, washed with water, with ethanol and with diethyl ether, and recrystallized from a mixture of dimethylformamide and water to give 2-benzyloxy-5-chloro-N-(tetrazol-5-yl)benzamide, (0.29 g), m.p. 256°-257° C. (with decomposition).

Provenance & Evidence