Benzoyl chloride → N-(2-Chloro-4-nitrophenyl)benzamide

A mixture of 2-chloro-4-nitroaniline (15.0 g, 86.9 mmol), triethylamine (13.3 ml, 95.6 mmol) and benzoyl chloride (11.1 ml, 95.6 mmol) were heated in toluene (200 ml) at reflux for 2 hours under an inert atmosphere. The reaction was allowed to cool to ambient temperature overnight, causing precipitation of a white solid. The solid was collected by suction filtration, washed with toluene (3×50 ml) and dried in vacuo. The crude product was taken up in dichloromethane (300 ml) and washed with 2.0 N aqueous hydrochloric acid (3×100 ml), water (100 ml), saturated aqueous sodium bicarbonate solution (3×100 ml) and water (100 ml). Drying of the organic layer over magnesium sulphate, followed by solvent evaporation in vacuo, yielded N-benzoyl 2-chloro-4-nitroaniline (6.83 g, 28% yield) as a yellow crystalline solid:

1. temperatureat reflux for 2 hours under an inert atmosphere
2. customprecipitation of a white solid
3. filtrationThe solid was collected by suction filtration
4. washwashed with toluene (3×50 ml)
5. customdried in vacuo
6. washwashed with 2.0 N aqueous hydrochloric acid (3×100 ml), water (100 ml), saturated aqueous sodium bicarbonate solution (3×100 ml) and water (100 ml)
7. dry with materialDrying of the organic layer over magnesium sulphate
8. customfollowed by solvent evaporation in vacuo

ORD record

ord-853e9f35a4f24838af3ffffde54adeb2

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709479B1