Reacción #7499

Ecuación de reacción

Dimethylaminopyridine

title compound

2-amino-3-methyl-N-(1-methylethyl)benzamide

triethylamine

acryloyl chloride

Acryloyl chloride

→

product

Rendimiento 52.4%

3-Methyl-N-(1-methylethyl)-2-[(1-oxo-2-propenyl)amino]benzamide

Rendimiento 52.4%

Disolventes

dichloromethane

HCl

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was warmed to ambient temperature
2. 2
   workup.STIRRINGThe mixture was stirred at ambient temperature for 0.5 h
3. 3
   Extracciónextracted twice with dichloromethane
4. 4
   SecadoThe organic extracts were dried (MgSO4)
5. 5
   Concentraciónconcentrated

Procedimiento

To a solution of the title compound of Step B (0.93 g, 4.8 mmol) in dichloromethane (10 mL) was added triethylamine (0.876 mL, 6.2 mmol) and the mixture was cooled to 0° C. Acryloyl chloride (0.433 mL, 5.3 mmol) was then added and the mixture was warmed to ambient temperature and stirred overnight. Dimethylaminopyridine (1.0 g, 7.7 mmol) was then added followed by acryloyl chloride (0.475 mL, 5.8 mmol). The mixture was stirred at ambient temperature for 0.5 h before being diluted with 1N HCl and extracted twice with dichloromethane. The organic extracts were dried (MgSO4) and concentrated to give the product of Step C (0.62 g) as a white solid.

Fuente