Oxalyl chloride → HCID 89536828, compound

Participants

Reaction Conditions

Reaction Steps

500 mg (2.31 mmol) of 2-chloro-5-methyl-3-(methylthio)benzoic acid and 320 mg (3.23 mmol) of 5-amino-1-methyltetrazole and a catalytic amount of 4-(dimethylamino)pyridine were dissolved in 10 ml of pyridine. 410 mg (3.23 mmol) of oxalyl chloride were then carefully added dropwise. After ten minutes, the mixture was stirred at 80° C. for 4 h. To bring the reaction to completion, another 137 mg (1.08 mmol) of oxalyl chloride were added at RT and the mixture was stirred at 80° C. for another 4 h. For work-up, the contents were cooled to RT and freed of the solvent on a rotary evaporator, and the residue was dissolved in dichloromethane. The solution was washed with saturated aqueous sodium bicarbonate solution and the organic phase was then freed of the solvent. The residue was purified chromatographically, giving 495 mg of 2-chloro-5-methyl-3-methylthio-N-(1-methyltetrazol-5-yl)benzamide.

Provenance & Evidence