Water → 2-(2,6-dichlorophenyl)-N-hydroxyethanimidoyl chloride

Participants

Reaction Steps

A solution of sodium hydroxide (0.672 g, 16.8 mmol) and hydroxylamine hydrochloride (1.17 g, 16.8 mmol) in water (11 mL) was added to a solution of (2,6-dichlorophenyl)acetaldehyde (2.78 g, 14.7 mmol) in ethanol (21 mL). The resulting solution was heated in an 83° C. oil bath overnight. The sample was concentrated and filtered. The resulting solid was dried with P2O5 in a vacuum oven at 45° C. under reduced pressure to provide the oxime as a mixture of isomers (2.21 g yield, 74%). A solution of (2,6-dichlorophenyl)acetaldehyde oxime (1.05 g, 4.82 mmol) in dimethylformamide (3.8 mL) was stirred as N-chlorosuccinimide (0.64 g, 4.82 mmol) was added and the resulting solution was allowed to stir for one hour. The solution was poured into water and extracted with ether. The organic layer was washed with brine, dried with magnesium sulfate, filtered and concentrated to yield the title compound (2.60 g, 77%). 1H NMR (DMSO-d6): 11.78 (s, 1H), 7.47 (d, J=8 Hz, 2H), 7.33 (t, J=8 Hz, 1H), 4.08 (s, 2H).

Provenance & Evidence