4-Toluenesulfonyl chloride → Benzeneacetonitrile, alpha-[[[(4-methylphenyl)sulfonyl]oxy]imino]-

Participants

Reaction Steps

A mixture of (Z)—N-hydroxybenzimidoyl cyanide (8 g, 55.1 mmol) and 4-methylbenzene-1-sulfonyl chloride (10.51 g, 55.1 mmol) in toluene (70 mL) was heated at reflux. After 2 h, the reaction was allowed to cool, diluted with ethyl acetate (100 mL) and washed with water (50 mL) and brine (50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to yield (Z)—N-(tosyloxy)benzimidoyl cyanide (10 g, 33.3 mmol, 60.4% yield) as a light yellow solid.

Provenance & Evidence