Dimethylformamide → 4-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoyl chloride

Participants

Reaction Steps

46 ml of thionyl chloride and 1 ml of DMF are added to a solution of 10.0 g of 4-(5-methyl-1,2,4-oxadiazol-3-yl)benzoic acid in 150 ml of toluene. The solution is heated under reflux for 5 hours. The solvent is removed, giving 4-(5-methyl-1,2,4-oxadiazol-3-yl)-benzoyl chloride, EI 222. Subsequent reaction with 9.3 g of 1-tert-butoxycarbonylpiperazine in 150 ml of dichloromethane and 48 ml of triethylamine gives, after customary work-up, tert-butyl 4-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoyl]piperazine-1-carboxylate, FAB 373.

Provenance & Evidence