Dichloromethane → 5-Methyl-2-nitrobenzoyl chloride

Participants

Reaction Steps

The reaction of 36.2 g of 5-methyl-2-nitrobenzoic acid and 41.6 g of phosphorus pentachloride in 150 ml of toluene gave a crude product which was treated with methylene chloride to give 5-methyl-2-nitrobenzoyl chloride as an oil. When 30 g of this acid chloride in 50 ml of tetrahydrofuran was added to a warm solution of 30.9 g of 5-aminotetrazole monohydrate in 600 ml of tetrahydrofuran and 30 ml of water, a precipitate formed quickly. This was allowed to stand for 1 hour, the white solid was separated by filtration, washed with water and air dried to give 5-methyl-2-nitro-N-(1H-tetrazol-5-yl)benzamide melting at about 278°-279° C.

Provenance & Evidence