N-Ethylaniline → N-ethyl-2-bromo-5-nitro-N-phenyl-benzamide

Temperature

23 °C

Oxalyl chloride (1.65 ml, 2.3 g, 18.3 mmol) was added dropwise to a solution of 2-bromo-5-nitrobenzoic acid (3 g, 12.2 mmol) in dichloromethane (12 ml). N,N-Dimethylformamide (0.01 ml) was added to the reaction mixture via syringe, the reaction mixture was stirred at 23° C. for 4 hour. The reaction mixture was concentrated in vacuo, and the residue was taken up in dichloromethane (24 ml), and DMAP (10 mg) and triethylamine (3.4 ml, 2.5 g, 24.3 mmol) were added. N-Ethylaniline (1.8 ml, 1.8 g, 14.6 mmol) was added over a 10 min period. After 18 hours at this temperature, 1:1 ethyl acetate/hexanes (30 ml) was added, and the organics were washed with 1N HCl (2-30 ml portions) and saturated aqueous sodium chloride (30 mL). The organics were dried over anhydrous sodium sulfate and concentrated. Purification of the residue by recrystallization from ethyl acetate/hexanes afforded N-ethyl-2-bromo-5-nitro-N-phenyl-benzamide (3.8 g, 60%).

1. concentrationThe reaction mixture was concentrated in vacuo
2. washthe organics were washed with 1N HCl (2-30 ml portions) and saturated aqueous sodium chloride (30 mL)
3. dry with materialThe organics were dried over anhydrous sodium sulfate
4. concentrationconcentrated
5. customPurification of the residue
6. customby recrystallization from ethyl acetate/hexanes

ORD record

ord-228bcdc97d7c481eabdb1d890b6e667c

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06958347B2