Reaktion #7499

Reaktionsgleichung

Dimethylaminopyridine

title compound

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

triethylamine

acryloyl chloride

Acryloyl chloride

→

product

Ausbeute 52.4%

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

Ausbeute 52.4%

Lösungsmittel

dichloromethane

HCl

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was warmed to ambient temperature
2. 2
   workup.STIRRINGThe mixture was stirred at ambient temperature for 0.5 h
3. 3
   Extraktionextracted twice with dichloromethane
4. 4
   TrocknenThe organic extracts were dried (MgSO4)
5. 5
   Einengenconcentrated

Vorschrift

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.

Quelle