Réaction #3500

Équation de réaction

water

sodium hydride

N-methoxy-p-chlorobenzamide

propargyl bromide

→

N-methoxy-N-propargyl-p-chlorobenzamide

Rendement 36.5%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températurein this order while being cooled with ice
2. 2
   TempératureThe mixture was heat-refluxed for 8 hours
3. 3
   workup.ADDITIONwas added to the reaction solution
4. 4
   Extractionthe mixture was extracted with ethyl acetate
5. 5
   AutreThe extract was dried
6. 6
   Concentrationconcentrated
7. 7
   Autrepurified by silica gel column chromatography

Mode opératoire

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.

Source