Reacción #2548

Ecuación de reacción

sodium iodide

sodium hydride

phthalimide

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

→

title compound

Rendimiento 77.6%

N-(2-Methoxyphenyl)-4-phthalimidomethylbenzamide

Rendimiento 77.6%

Disolventes

DMF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat room temperature
2. 2
   workup.STIRRINGAfter 2 hours of stirring at 80° C.
3. 3
   Otrosubsequent removal of the solvent
4. 4
   Otroby evaporation
5. 5
   workup.ADDITIONthe resulting residue was mixed with water (10 ml)
6. 6
   Extracciónextracted with an ethyl acetate-methylene chloride (1:2) mixture solution
7. 7
   LavadoThe resulting organic layer was washed with water and saturated brine
8. 8
   Secadodried on anhydrous magnesium sulfate
9. 9
   OtroThereafter, the solvent was removed by evaporation
10. 10
    Lavadowashed with ether

Procedimiento

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.

Fuente