Réaction #2548

Équation de réaction

sodium iodide

sodium hydride

phthalimide

4-chloromethyl-N-(2-methoxyphenyl)benzamide

→

title compound

Rendement 77.6%

N-(2-Methoxyphenyl)-4-phthalimidomethylbenzamide

Rendement 77.6%

Solvants

DMF

THF

Conditions de réaction

Traitement

1. 1
   Autreat room temperature
2. 2
   workup.STIRRINGAfter 2 hours of stirring at 80° C.
3. 3
   Autresubsequent removal of the solvent
4. 4
   Autreby evaporation
5. 5
   workup.ADDITIONthe resulting residue was mixed with water (10 ml)
6. 6
   Extractionextracted with an ethyl acetate-methylene chloride (1:2) mixture solution
7. 7
   LavageThe resulting organic layer was washed with water and saturated brine
8. 8
   Séchagedried on anhydrous magnesium sulfate
9. 9
   AutreThereafter, the solvent was removed by evaporation
10. 10
    Lavagewashed with ether

Mode opératoire

In an atmosphere of argon, phthalimide (150 mg, 1.0 mmol) was dissolved in THF (10 ml) to which was subsequently added sodium hydride (44 mg, 60%, 1.1 mmol) at room temperature. After 40 minutes of stirring at the same temperature, to this was added a DMF solution (5 ml) containing 4-chloromethyl-N-(2-methoxyphenyl)benzamide (276 mg, 1.0 mmol) and a catalytically effective amount of sodium iodide. After 2 hours of stirring at 80° C. and subsequent removal of the solvent by evaporation, the resulting residue was mixed with water (10 ml) and extracted with an ethyl acetate-methylene chloride (1:2) mixture solution. The resulting organic layer was washed with water and saturated brine and dried on anhydrous magnesium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was subjected to a silica gel column chromatography (methylene chloride-ether:hexane=2:1) and then washed with ether to obtain 300 mg (77.6%) of the title compound in the form of colorless solid.

Source