Hydrazine hydrate (1:1) → 4-ethoxy-N-(2-hydrazino-2-oxoethyl)-N-(4-methylphenyl)benzenesulfonamide

Participants

Reaction Steps

The crude carboxylic acid methyl ester, e.g. methyl{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}acetate (3.816 g, 10.5 mmol), was dissolved in MeOH (30 mL). Hydrazine hydrate was added (3.3 mL). The reaction mixture was stirred overnight at room temperature. A white precipitate was formed. It was isolated by filtration and rinsed with cold MeOH. From mother liquors some more compound could be recovered, affording the desired product, e.g. 4-ethoxy-N-(2-hydrazino-2-oxoethyl)-N-(4-methylphenyl)benzenesulfonamide (2.745 g, 72%) as a colorless solid in 99.8% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Provenance & Evidence