Ammonium Hydroxide → N-(5-Fluoro-2-methyl-4-sulfamoylphenyl)acetamide

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Reaction Steps

The moist 2-acetamido-4-fluoro-5-chlorosulphonyltoluene (3) was heated in 650 ml of concentrated ammonium hydroxide until it reached 50°. The resulting solution was cooled and extracted with ethyl acetate, (10×1000 ml). The extracts were combined and concentrated in vacuo, to give a solid. The latter was purified by dissolving the solid in 350 ml of a 20% aqueous solution of sodium hydroxide, filtering this mixture and acidifying the filtrate with concentrated hydrochloric acid. The precipitate, which separated out, was recovered, then dried; yield: 32.9 g (23.4%); m.p.: 205-207°; literature:1 m.p.: 206-208°.

Provenance & Evidence