Thionyl Chloride → 4-[(Methylsulfonyl)amino]benzoyl chloride

Participants

Reaction Steps

To 600 ml of thionyl chloride at 0° C. is added 150 g (0.63 mole) of 4-[(methylsulfonyl)amino]benzoic acid sodium salt under a nitrogen atmosphere and the reaction is refluxed for 40 hours. The excess thionyl chloride is removed in vacuo and the crude product triturated with toluene and evaporated. After dissolving the solid in tetrahydrofuran, charcoal is added, and the mixture filtered through Celite. Concentration in vacuo provides a solid which is then slurried with cold ether and collected by filtration. Drying for 18 hours in vacuo provides 133 g of the title compound.

Provenance & Evidence