Reaktion #972839

Reaktionsgleichung

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

Lösungsmittel

water

Water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle