반응 #2548

반응 방정식

sodium iodide

sodium hydride

phthalimide

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

→

title compound

수율 77.6%

N-(2-Methoxyphenyl)-4-phthalimidomethylbenzamide

수율 77.6%

용매

DMF

THF

반응 조건

후처리

1. 1
   기타at room temperature
2. 2
   workup.STIRRINGAfter 2 hours of stirring at 80° C.
3. 3
   기타subsequent removal of the solvent
4. 4
   기타by evaporation
5. 5
   workup.ADDITIONthe resulting residue was mixed with water (10 ml)
6. 6
   추출extracted with an ethyl acetate-methylene chloride (1:2) mixture solution
7. 7
   세척The resulting organic layer was washed with water and saturated brine
8. 8
   건조dried on anhydrous magnesium sulfate
9. 9
   기타Thereafter, the solvent was removed by evaporation
10. 10
    세척washed with ether

실험 절차

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.

출처