Реакция #7499

Уравнение реакции

Dimethylaminopyridine

title compound

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

triethylamine

acryloyl chloride

Acryloyl chloride

→

product

Выход 52.4%

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

Выход 52.4%

Растворители

dichloromethane

HCl

Условия реакции

Обработка

1. 1
   Температураthe mixture was warmed to ambient temperature
2. 2
   workup.STIRRINGThe mixture was stirred at ambient temperature for 0.5 h
3. 3
   Экстракцияextracted twice with dichloromethane
4. 4
   СушкаThe organic extracts were dried (MgSO4)
5. 5
   Концентрированиеconcentrated

Методика

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.

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