Dimethylformamide → 2-Fluoro-5-nitro-N-(phenylmethyl)benzamide

Temperature

0 °C

To a suspension of 2-fluoro-5-nitrobenzoic acid (313 mg) in dichloromethane (4 mL) were added thionyl chloride (0.17 mL) and dimethylformamide (0.05 mL), and the mixture was heated for 36 hours under reflux. After evaporation of the solvent, the residue was dissolved in dichloromethane (4 mL). To this solution were added benzylamine (0.19 mL) and triethylamine (0.47 mL), and the mixture was stirred for 30 minutes at 0° C. After evaporation of the solvent, the residue was dissolved in ethyl acetate and washed successively with diluted hydrochloric acid, an aqueous sodium bicarbonate solution and brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The resulting residue was triturated with diisopropyl ether to give N-benzyl-2-fluoro-5-nitrobenzamide (436 mg) as a solid substance.

1. temperaturethe mixture was heated for 36 hours
2. temperatureunder reflux
3. customAfter evaporation of the solvent
4. dissolutionthe residue was dissolved in dichloromethane (4 mL)
5. additionTo this solution were added benzylamine (0.19 mL) and triethylamine (0.47 mL)
6. customAfter evaporation of the solvent
7. dissolutionthe residue was dissolved in ethyl acetate
8. washwashed successively with diluted hydrochloric acid
9. dry with materialThe organic layer was dried over sodium sulfate
10. customevaporated in vacuo
11. customThe resulting residue was triturated with diisopropyl ether

ORD record

ord-de41f020eb0344cfb69928742e3b8d7e

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06384080B1