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

HRID 501877Notes

Reaction equation

HRID 501877 reaction equation
[OH-].[K+].[CH3:3][N:4]([CH3:19])[CH:5]=[CH:6][C:7]([C:9]1[CH:10]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:12]=[CH:13][CH:14]=1)=[O:8].[CH2:20](I)[CH3:21]>CN(C)C=O>[CH3:19][N:4]([CH3:3])[CH:5]=[CH:6][C:7]([C:9]1[CH:10]=[C:11]([N:15]([CH2:20][CH3:21])[C:16](=[O:18])[CH3:17])[CH:12]=[CH:13][CH:14]=1)=[O:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 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

36.2 gm Powdered potassium hydroxide was added portion wise to a clear solution of a mixture of 100 gm N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl] acetamide and 70 ml ethyl iodide in 1000 ml of dimethyl formamide at 39°-42° C. over 60 min. the reaction mixture was stirred for 6 hrs. after completion, the reaction mixture was quenched in water and extracted in dichloromethane. The dichloromethane layer was washed with water, dried over sodium sulphate and concentrated to get oil, which upon trituration in hexane gave a solid product which was filtered and dried at 40° C. under vacuum to give the title compound.

Workup

  1. customafter completion, the reaction mixture was quenched in water
  2. extractionextracted in dichloromethane
  3. washThe dichloromethane layer was washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customto get oil, which upon trituration in hexane
  7. customgave a solid product which
  8. filtrationwas filtered
  9. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-1a8a09a3701544a8b87c1c39328e56e9
Source dataset
uspto-grants-2010_08
Patent number
US07772394B2

Reaction notes

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