Development of an Efficient Synthetic Method for Nitrogen-Containing Heterocyclic Primary Sulfonamides.

A gas-free, one-pot synthesis of heterocyclic primary sulfonamides from heterocyclic thiols is described. This method employs sodium hypochlorite pentahydrate as a solid chlorinating source and aqueous ammonia as a nitrogen source, avoiding hazardous chlorine and ammonia gases. The protocol was applied to a range of pyrimidine, pyridine, benzothiazole, and tetrazole derivatives. The utility of this method was further demonstrated by 15N-labeling and multigram-scale synthesis.