Hydrochloric Acid → HCID 178450145, compound

Participants

Reaction Steps

A stirred solution of 1-benzyl-3'-butyryl-2'-hydroxy-5'-methyl-1H-tetrazole-5-carboxanilide in dichloromethane (75 ml), heated at reflux, was treated with anhydrous aluminium chloride (2.2 g) over a period of 15 minutes. After heating and stirring for a further hour, the mixture was cooled and treated with aqueous hydrochloric acid (2 N; 50 ml). The resulting suspension was heated at reflux with stirring for 15 minutes and then cooled. The precipitated solid was filtered off and combined with a residue which was subsequently obtained by evaporation of the dichloromethane layer of the filtrate. This combined solid was digested in aqueous sodium carbonate solution (2 N) at 90° C., then filtered to remove insoluble material and acidified by treatment with concentrated hydrochloric acid. Recrystallisation from a mixture of dimethylformamide and water gave 3'-butyryl-2'-hydroxy-5'-methyltetrazole-5-carboxanilide (0.78 g), m.p. 231°-233° C. (with decomposition).

Provenance & Evidence