反応 #2548

反応方程式

sodium iodide

sodium hydride

phthalimide

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

→

title compound

収率 77.6%

N-(2-Methoxyphenyl)-4-phthalimidomethylbenzamide

収率 77.6%

溶媒

DMF

THF

反応条件

後処理

1. 1
   その他at room temperature
2. 2
   workup.STIRRINGAfter 2 hours of stirring at 80° C.
3. 3
   その他subsequent removal of the solvent
4. 4
   その他by evaporation
5. 5
   workup.ADDITIONthe resulting residue was mixed with water (10 ml)
6. 6
   抽出extracted with an ethyl acetate-methylene chloride (1:2) mixture solution
7. 7
   洗浄The resulting organic layer was washed with water and saturated brine
8. 8
   乾燥dried on anhydrous magnesium sulfate
9. 9
   その他Thereafter, the solvent was removed by evaporation
10. 10
    洗浄washed with ether

実験手順

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.

出典