Methane → HCID 178497856, compound

Participants

Reaction Steps

1-Benzyl-2'-hydroxy-3'-methoxycarbonyl-5'-methyl-1H-tetrazole-5-carboxanilide (3.0 g) was added, with stirring, to a suspension of anhydrous aluminium chloride (3.6 g) in dichloromethane (150 ml). After stirring and heating at reflux for 150 minutes, the mixture was poured into a mixture of ice (100 g), aqueous hydrochloric acid (2 N; 100 ml) and ethyl acetate (100 ml), and stirring was continued for a further period of 2 hours. The remaining insoluble material was filtered off and the organic layer was washed with water (3×20 ml) and dried over anhydrous sodium sulphate. Evaporation of the solvent gave a yellow solid, which was then digested in aqueous potassium bicarbonate solution (5% w/v; 100 ml), and the resulting solution was treated with charcoal and filtered. Acidification of the filtrate gave a solid, which was recrystallised from nitromethane to give 2'-hydroxy-3'-methoxycarbonyl-5'-methyltetrazole-5-carboxanilide (1.2 g), m.p. 238°-240° C.

Provenance & Evidence