Reaktion #2548

Reaktionsgleichung

sodium iodide

sodium hydride

phthalimide

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

→

title compound

Ausbeute 77.6%

N-(2-Methoxyphenyl)-4-phthalimidomethylbenzamide

Ausbeute 77.6%

Lösungsmittel

DMF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat room temperature
2. 2
   workup.STIRRINGAfter 2 hours of stirring at 80° C.
3. 3
   Sonstigesubsequent removal of the solvent
4. 4
   Sonstigeby evaporation
5. 5
   workup.ADDITIONthe resulting residue was mixed with water (10 ml)
6. 6
   Extraktionextracted with an ethyl acetate-methylene chloride (1:2) mixture solution
7. 7
   WaschenThe resulting organic layer was washed with water and saturated brine
8. 8
   Trocknendried on anhydrous magnesium sulfate
9. 9
   SonstigeThereafter, the solvent was removed by evaporation
10. 10
    Waschenwashed with ether

Vorschrift

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.

Quelle