Thionyl Chloride → 6-Amino-7-chloro-benzo[1,2,5]thiadiazole-5-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a suspension of 20 mg (93 mmol) of 2,4,5-triamino-3-chloro-benzoic acid methyl ester in 1 ml of acetonitrile, is added 32 ml (0.19 mmol) of N,N-diisopropylethylamine followed by 9 ml (0.13 mmol) of thionyl chloride. The mixture is stirred at 80° C. over the night. Then, 32 ml of N,N-diisopropylethylamine is added again as well as 9 ml of thionyl chloride and the mixture is again stirred for 5 hours at a temperature of 80° C. The solvent is evaporated and the residue is suspended in EtOAc. After filtration, EtOAc is evaporated and 18 mg (73.9 mmol, 80%) of a yellowish-brown solid is obtained. LC/MS: 244/246 (M+1)+.

Provenance & Evidence