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

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Reaction Steps

3-Dimethylamino-5-pentafluorosulfanylbenzoic acid (1.0 g) was dissolved in methylene chloride (60 ml). Thionyl chloride (5 ml) was added with stirring and the mixture was stirred at RT for 2 h. To complete the reaction, it was subsequently heated at reflux for 3 h. After cooling, the solvent was stripped off, and the residue was dissolved in methylene chloride (50 ml), treated with N,O-dimethylhydroxylamine hydrochloride and Hünig's base (1 ml) was added. After stirring for one hour, the solvent was stripped 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 reacted directly in the next stage.

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