Reacción #3500

Ecuación de reacción

water

sodium hydride

N-methoxy-p-chlorobenzamide

propargyl bromide

→

N-methoxy-N-propargyl-p-chlorobenzamide

Rendimiento 36.5%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturain this order while being cooled with ice
2. 2
   TemperaturaThe mixture was heat-refluxed for 8 hours
3. 3
   workup.ADDITIONwas added to the reaction solution
4. 4
   Extracciónthe mixture was extracted with ethyl acetate
5. 5
   OtroThe extract was dried
6. 6
   Concentraciónconcentrated
7. 7
   Otropurified by silica gel column chromatography

Procedimiento

0.22 g of sodium hydride (60% in oil) was suspended in 10 ml of tetrahydrofuran, and 1.0 g of N-methoxy-p-chlorobenzamide and 0.68 g of propargyl bromide were added thereto in this order while being cooled with ice. The mixture was heat-refluxed for 8 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried, concentrated and purified by silica gel column chromatography to obtain 0.44 g of N-methoxy-N-propargyl-p-chlorobenzamide.

Fuente