Sodium Iodide → 2-Amino-5-cyano-N,3-dimethylbenzamide

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 Reference Example 1) (99% purity, 5.0 g, 0.02 mol) and mesitylene (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 sodium cyanide powder (CyPlus®, 1.40 g, 0.027 mol, assuming 95% purity), copper(I) cyanide (0.27 g, 0.003 mol, 99% purity), sodium iodide (0.45 g, 0.003 mol, 99% purity) and 1-butyl-1H-imidazole (1.9 g, 0.015 mol, 98% purity) were added. The mixture was heated at reflux (about 167-168° C.) for 6 h and then allowed to cool overnight. Water (20 mL) was added dropwise to the reaction mixture over 5 minutes while stirring. After stirring for an additional 1 h, the reaction mixture was filtered, and the solid collected was washed successively with water (3×10 mL), mesitylene (10 mL) and dried to a constant weight in a vacuum-oven at 55° C. to give the title compound as a light yellow solid (3.4 g).

1. customA 100-mL three-necked flask equipped with a mechanical stirrer
2. temperaturewhile maintaining a flow of nitrogen through a gas inlet line
3. temperatureThe mixture was heated
4. temperatureat reflux (about 167-168° C.) for 6 h
5. temperatureto cool overnight
6. stirringwhile stirring
7. stirringAfter stirring for an additional 1 h
8. filtrationthe reaction mixture was filtered
9. customthe solid collected
10. washwas washed successively with water (3×10 mL), mesitylene (10 mL)
11. customdried to a constant weight in a vacuum-oven at 55° C.

ORD record

ord-e8120705ab20422aba5d1522a6ef0b9c

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242279B2