Chloroacetic Acid → 2-chloro-N-(3,4-dichlorophenyl)acetamide

Participants

Reaction Steps

3,4-Dichloroaniline (8.10 g, 50.0 mmol) was dissolved in THF (50 mL) To the solution was added anhydrous chloroacetic acid (9.40 g, 55.0 mmol), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and to the concentrate was added ethyl acetate, (100 mL). The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (50 mL, 20 mL×2), saturated sodium chloride solution (20 mL), successively, dried over magnesium sulfate and concentrated under reduced pressure. To the concentrate was added diisopropyl ether (30 mL) and the resulting precipitates were collected by filtration. The precipitates were washed with diisopropyl ether (10 mL×3), and dried under reduced pressure to give the titled compound (8.08 g) as white crystals. The filtrate was concentrated under reduced pressure. To the concentrate was added diisopropyl ether/hexane (1/1) mixed solvent (30 mL), and the precipitates was collected by filtration. The precipitates were washed with diisopropyl ether/hexane (1/1) mixed solvent (10 mL×3), and dried under reduced pressure to give the titled compound (3.0 g) as white crystals. Yield (11.09 g, 93%, 46.5 mmol).

Provenance & Evidence