Chlorobenzene → 2-Amino-5-cyano-N,3-dimethylbenzamide

Participants

Reaction Steps

A 100-mL three-necked flask equipped with a mechanical stirrer, thermometer and condenser was charged with 2-amino-5-bromo-N,3-dimethylbenzamide (prepared by the method of Example 1) (99.1% purity, 5.0 g, 0.02 mol) and chlorobenzene (20 g) while maintaining a flow of nitrogen through a gas inlet line connected to the condenser. The reaction mixture was stirred at room temperature, and powdered sodium cyanide (powdered just prior to use) (1.25 g, 0.024 mol, assuming 95% purity), copper(I) iodide (0.57 g, 0.003 mol) and N,N′-dimethylethylenediamine (1.51 g, 0.017 mol) were added. The mixture was heated at reflux (about 130° C.) for 4.5 h and then cooled to 25° C., and water (20 mL) was added over 5 minutes, and the resulting mixture was stirred for 30 minutes. The mixture was filtered, and the solid collected was washed with water (2×10 mL) and chlorobenzene (10 mL), and then dried to a constant weight in a vacuum-oven at 50° C. to give the title compound (3.6 g) as an off-white solid melting at 202-203° C.

Provenance & Evidence