Water → N-hydroxybenzenecarboximidoyl chloride

Participants

Reaction Steps

N-chlorosuccinimide (5.50 g, 41.3 mmol) was added in portions to a solution of benzaldehyde oxime (5.0 g, 41.3 mmol) in DMF (34 ml) such that the temperature did not rise above 35° C. The mixture was stirred at ambient temperature for 2 hours and then cooled with an ice bath. Water was added and the aqueous mixture extracted with ether. The organics were combined, washed with water and brine, dried (MgSO4) and the solvent removed by evaporation to give the title compound (6.43 g, 100%) as an oil. NMR (CDCl3): 7.4 (m, 3H), 7.8 (d, 2H), 8.9 (bs, 1H).

Provenance & Evidence