Carbon Tetrachloride → 5-Chloro-2-nitrobenzoyl chloride

Participants

Reaction Steps

Reaction of 100 g of 5-chloro-2-nitrobenzoic acid and 103.3 g of phosphorus pentachloride in 400 ml of cyclohexane at reflux for 80 minutes followed by treatment of the crude product 3 times with carbon tetrachloride gave 5-chloro-2-nitrobenzoyl chloride. A solution of the acid chloride in 50 ml of tetrahydrofuran was added to a warm solution of 91.3 g of 5-aminotetrazole monohydrate in 500 ml of tetrahydrofuran and 20 ml of water. A precipitate formed, and the mixture was allowed to stand for 4 hours. It was then diluted with water and the solid was separated by filtration and air dried to give 5-chloro-2-nitro-N-(1H-tetrazol-5-yl)benzamide melting at about 268°-269° C., after recrystallization from dimethylformamide.

Provenance & Evidence