Reaktion #972833

Reaktionsgleichung

sodium cyanide

1-butyl-1H-imidazole

Ethylenediamine

sodium hydroxide sodium hypochlorite

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

mesitylene

→

title compound

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

Lösungsmittel

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 7 h
6. 6
   TemperaturAfter cooling overnight
7. 7
   workup.STIRRINGstirring
8. 8
   workup.STIRRINGstirring
9. 9
   workup.WAITwas continued 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 sodium cyanide (ground to a powder just prior to use) (6.2 g, 0.121 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, 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 7 h, while venting through the scrubber. After cooling overnight, water (100 mL) was added to the reaction mixture and stirring was continued for 1 h. Ethylenediamine (0.09 g, about 0.015 mol, 99% purity) was added to the mixture, and stirring was 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 brown solid (18.3 g).

Quelle