4-Amino-3-methylbenzenesulfonic acid → Pyridinium 4-(acetylamino)-3-methylbenzenesulfonate

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Reaction Steps

For example, commercially available 2-aminotoluene-5-sulfonic acid was allowed to react with acetic anhydride in pyridine to afford pyridinium 4-(acetylamino)-3-methylbenzenesulfonate (Scheme V). The resulting salt was then allowed to react with sodium hydroxide to afford the corresponding sodium salt, sodium 4-(acetylamino)-3-methylbenzenesulfonate. The salt was then allowed to react with thionyl chloride to afford the intermediate sulfonyl chloride, followed by reaction with ammonia and subsequent deprotection by reaction with aqueous hydrochloric acid in ethanol to afford the desired sulfonamide.

Provenance & Evidence