反応 #972839

反応方程式

sodium cyanide

1-butyl-1H-imidazole

sodium hydroxide sodium hypochlorite

2-amino-5-bromo-N,3-dimethylbenzamide

mesitylene

→

title compound

2-amino-5-cyano-N,3-dimethylbenzamide

溶媒

water

Water

反応条件

後処理

1. 1
   その他A 500-mL four-necked flask equipped with a mechanical stirrer
2. 2
   workup.ADDITIONthermocouple, condenser, side-arm addition funnel
3. 3
   温度while maintaining an atmosphere of nitrogen through a gas inlet line
4. 4
   温度The reaction mixture was heated
5. 5
   温度at reflux (about 166-170° C.) for 6 h
6. 6
   温度to cool overnight
7. 7
   workup.STIRRINGstirring
8. 8
   workup.STIRRINGstirring
9. 9
   workup.WAITcontinued for an additional 15 minutes
10. 10
    ろ過The mixture was filtered
11. 11
    その他the solid collected
12. 12
    洗浄was washed with water (3×50 mL), mesitylene (50 g)
13. 13
    その他dried to a constant weight in a vacuum-oven at 55° C.

実験手順

A 500-mL four-necked flask equipped with a mechanical stirrer, thermocouple, condenser, side-arm addition funnel and sodium hydroxide/sodium hypochlorite scrubber was charged with 2-amino-5-bromo-N,3-dimethylbenzamide (prepared by the method of Reference Example 1) (24.6 g, 0.10 mol, 99% purity) and mesitylene (100 g) while maintaining an atmosphere of nitrogen through a gas inlet line connected to the condenser. The reaction mixture was stirred at room temperature, and granular sodium cyanide (Alfa Aesar®, 7.7 g, 0.15 mol, assuming 95% purity), copper(I) iodide (2.9 g, 0.015 mol, 98% purity) and 1-butyl-1H-imidazole (10.8 g, 0.085 mol, 98% purity) were added to the reaction mixture, after which time the nitrogen inlet line was attached directly to the reaction flask. The reaction mixture was heated at reflux (about 166-170° C.) for 6 h, while venting through the scrubber and then allow to cool overnight. Water (100 mL) was added to the reaction mixture and stirring was continued for 45 minutes. More water (25 mL) was added to the reaction mixture and stirring continued for an additional 15 minutes. The mixture was filtered, and the solid collected was washed with water (3×50 mL), mesitylene (50 g) and dried to a constant weight in a vacuum-oven at 55° C. to give the title compound as a light yellow solid (16.8 g).

出典