4-Chloroaniline → Benzamide, 5-chloro-N-(4-chlorophenyl)-2-nitro-

Temperature

0 °C

To a solution of 5-chloro-2-nitrobenzoyl chloride (23 g, 100 mmol) in methylene chloride (200 mL) at 0° C. was added triethylamine (16 mL, 115 mmol), followed by 4-chloroaniline (14 g, 110 mmol). The mixture was stirred for 20 minutes at 0° C., then warmed to ambient temperature. After 5 hours, the mixture was concentrated of all volatiles in vacuo. The residual solid was dissolved in ethyl acetate (400 mL) and washed with water (200 mL), 1M hydrochloric acid (2×200 mL), 1M sodium bicarbonate (200 mL) and brine (200 mL) and dried over MgSO4. Concentration and drying in vacuo afforded 30 g (93% yield) of N-(4-chlorophenyl)-5-chloro-2-nitrobenzamide; NMR (CDCl3) 8.1 (d, 1), 7.7 (br, 1), 7.6 (m, 2), 7.5 (d, 2), 7.3 (d, 2) ppm.

1. temperaturewarmed to ambient temperature
2. waitAfter 5 hours
3. concentrationthe mixture was concentrated of all volatiles in vacuo
4. dissolutionThe residual solid was dissolved in ethyl acetate (400 mL)
5. washwashed with water (200 mL), 1M hydrochloric acid (2×200 mL), 1M sodium bicarbonate (200 mL) and brine (200 mL)
6. dry with materialdried over MgSO4
7. concentrationConcentration
8. customdrying in vacuo

ORD record

ord-592cee0fce8a4b788aab33340f97aa5f

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06498185B1