Ammonia → 3-Chloropyridine-2-sulfonamide

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Reaction Steps

The halopyridine sulfonamide of the present invention is prepared in a two-step process. In step one, benzyl mercaptan is dissolved in a solvent such as dimethylformamide or dimethylsulfoxide, mixed with 2,3-dichloropyridine and heated at about 50°-100° C. for about 2-6 hours. The residue is taken up in a solvent and distilled to give the resulting product, 3-chloro-2-(phenylmethyl)thio)pyridine. In step two, the halophenylmethylthiopyridine prepared in step one is converted by oxidative chlorination to a halopyridine sulfonyl chloride upon exposure to chlorine. The resulting sulfonyl chloride compound is reacted with aqueous ammonia for about 16 hours. The mixture is then acidified to a pH of about 5 and extracted with a suitable solvent, preferably ethyl acetate, and dried for 3-5 hours to yield the novel product, 3-chloro-2-pyridine sulfonamide. The product of the present invention is a colorless, needle-like, crystalline solid with a melting point of 128°-130° C. It is soluble in the usual organic solvents and in warm water.

Provenance & Evidence