Hydrochloric Acid → Benzenesulfonylbenzisothiazolone

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Reaction Steps

31.44 G. (0.2 mole) of benzenesulfonamide was dissolved in 80 ml. of dry pyridine to obtain a clear, straw-colored solution, which was placed in a cold water bath. To this pyridine solution was added the carbon tetrachloride solution produced in Part B above. An exothermic reaction ensued with formation of a white slurry, which was stirred at ambient temperature for 45 minutes and then poured into 600 ml. of 2N hydrochloric acid. The aqueous phase of the resultant mixture was decanted from the lower organic phase, which was cooled in ice water and filtered to remove carbon tetrachloride. The white solid thus obtained was slurried in 600 ml. of hot acetic acid, cooled and filtered to obtain a white solid, which was dried under vacuum to yield 49.7 g. of product having an infra-red spectrum consistent with the expected structure. The ultraviolet spectrum of the product in methanol showed peaks at 202 nm (ε=17,000), 232 nm. (ε=31,000) and 332 nm. (ε=4,000).

Provenance & Evidence