Sodium Azide → 3-Chloro-N-isopropyl-5-methoxy-N-[2-(1-methyl-1H-tetrazol-5-yl)ethyl]-benzamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-chloro-N-isopropyl-5-methoxy-N-(2-methylcarbamoyl-ethyl)-benzamide (0.312 g) in anhydrous dichloromethane (5.0 ml) was added sodium azide (0.065 g) and the mixture cooled to 0° C. Trifluoromethanesulphonic anhydride (0.200 ml) was added and the reaction stirred at room temperature for 18 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was removed and the organic layer dried with brine and over sodium sulphate and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with ethyl acetate:petroleum ether (4:1 v/v); to give the title compound as a white solid (0.121 g).

Provenance & Evidence