Hydrochloric Acid → 4-chloro-N-hydroxybenzene-1-carbonimidoyl chloride

Participants

Reaction Steps

To a solution of 4-chloro-benzaldehyde oxime (20 g, 0.13 mol) in anhydrous dimethylformamide (80 ml) was added N-chlorosuccinimide (3.51 g, 0.03 mol, 0.2 eq) at room temperature. Subsequently, HCl gas drawn from the headspace of concentrated hydrochloric acid was bubbled through the reaction mixture. Then, additional N-chlorosuccinimide (14.06 g, 0.11 mol, 0.8 eq) was then added in four portions and the mixture was stirred at room temperature for twenty hours before it was poured into ice-water (200 ml) and extracted twice with methyl t-butyl ether. The combined organic layers were washed with water and brine, and then dried and concentrated to give the title compound as a white solid (23.26 g): 1H NMR (CDCl3, 200 MHz): δ=7.97 (s, 1H), 7.77 (m, 2H), 7.36 (m, 2 H). 13C NMR (CDCl3, 50 MHz): δ=139.37, 137.10, 130.99, 128.94, 128.57

Provenance & Evidence