Thionyl Chloride → 3-Dimethylamino-N-methoxy-N-methyl-5-pentafluorosulfanylbenzamide

Participants

Reaction Steps

3-Dimethylamino-5-pentafluorosulfanylbenzoic acid (1.0 g) was dissolved in methylene chloride (60 ml). Thionyl chloride (5 ml) was added while stirring and the mixture was stirred at RT for 2 h. To complete the reaction, the mixture was subsequently heated to reflux for 3 h. After cooling, the solvent was drawn off, the residue was dissolved in methylene chloride (50 ml), and N,O-dimethylhydroxylamine hydrochloride (315 mg) and Hünig's base (1 ml) were added. After stirring for one hour, the solvent was drawn off, and the residue was taken up with ethyl acetate and washed 5 times with water. The organic phase was dried with magnesium sulfate, filtered and concentrated. 980 mg of the title compound were obtained, which were converted directly in the next stage.

Provenance & Evidence