Chlorosulfonic acid → HCID 59893774, compound

Participants

Reaction Steps

At −5° C., chlorosulfonic acid (0.22 mL, 3.33 mmol) was slowly added to a chloroform solution (10 mL) of 3,4,5-trimethoxyaniline (1.83 g, 10 mmol). After 1 hour at 25° C., the suspension was filtered, and the solid was washed with CH2Cl2. The residue was dissolved in Na2CO3 solution (0.5M, 20 mL), which was washed with ethyl ether (2×20 mL). The aqueous solution was concentrated to give a solid, which was extracted with boiling ethanol (20 mL). After evaporation of ethanol, the solid (200 mg) was treated with PCl5 (200 mg) in refluxing benzene (15 mL). The precipitate was filtered off and the filtrate was concentrated. The residue was purified by column chromatography (50% EtOAc in hexanes), affording 56 mg (5% yield) of the sulfamoyl chloride as a off-white solid.

Provenance & Evidence