Iodoethane → N-(3-(3-(Dimethylamino)-1-oxo-2-propenyl)phenyl)-N-ethylacetamide

HRID 501879Notes

Reaction equation

HRID 501879 reaction equation
C[O-].[Na+].[CH3:4][N:5]([CH3:20])[CH:6]=[CH:7][C:8]([C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[CH:13]=[CH:14][CH:15]=1)=[O:9].[CH2:21](I)[CH3:22]>CN(C)C=O>[CH3:20][N:5]([CH3:4])[CH:6]=[CH:7][C:8]([C:10]1[CH:11]=[C:12]([N:16]([CH2:21][CH3:22])[C:17](=[O:19])[CH3:18])[CH:13]=[CH:14][CH:15]=1)=[O:9]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10942334Sodium MethoxideHCID 53412415N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamide

Product 1

HCID 53395302N-(3-(3-(Dimethylamino)-1-oxo-2-propenyl)phenyl)-N-ethylacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

17.5 gm Sodium methoxide was added portion wise to a clear solution of 50 gm N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]-phenyl] acetamide and 85 gm ethyl iodide in 500 ml dimethyl formamide. After 6 hrs of stirring at room temperature, the reaction mass was quenched in 5 liters of water and extracted in dichloromethane. The dichloromethane layer was washed with water, dried over sodium sulphate and concentrated under vacuum to get oil, which upon trituration in hexane gave the title product as a solid.

Workup

  1. customthe reaction mass was quenched in 5 liters of water
  2. extractionextracted in dichloromethane
  3. washThe dichloromethane layer was washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum
  6. customto get oil, which upon trituration in hexane

Sources & evidence

ORD record
ord-743d668e962640679b910f8e9d134778
Source dataset
uspto-grants-2010_08
Patent number
US07772394B2

Reaction notes

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