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

HRID 501878Notes

Reaction equation

HRID 501878 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[CH3:7][N:8]([CH3:23])[CH:9]=[CH:10][C:11]([C:13]1[CH:14]=[C:15]([NH:19][C:20](=[O:22])[CH3:21])[CH:16]=[CH:17][CH:18]=1)=[O:12].C(I)C.CCCCCC>CN(C)C=O.ClCCl>[CH3:23][N:8]([CH3:7])[CH:9]=[CH:10][C:11]([C:13]1[CH:14]=[C:15]([N:19]([CH2:1][CH3:2])[C:20](=[O:22])[CH3:21])[CH:16]=[CH:17][CH:18]=1)=[O:12]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8058HexaneHCID 23665647Potassium tert-butoxideHCID 53412415N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

4.25 gm of Potassium tert-butoxide was added portion wise to a clear solution of 5 gm N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]-phenyl] acetamide in 50 ml dimethyl formamide. A solution of 5.25 gm Ethyl iodide in 20 ml dimethyl formamide was added drop wise over 3 hrs. at 35° C.-40° C. The reaction mass was stirred for 6 hrs and then quenched in 300 ml of water and extracted in dichloromethane. The organic layer was washed with water, dried over sodium sulphate and concentrated under vacuum to get oil, which was dissolved in 5 ml dichloromethane and 50 ml hexane was added to precipitate the product. The solids obtained was filtered and washed with hexane and dried in vacuum tray dryer at 35° C. for 6 hrs.

Workup

  1. customat 35° C.-40° C
  2. customquenched in 300 ml of water
  3. extractionextracted in dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customto get oil, which
  8. customto precipitate the product
  9. customThe solids obtained
  10. filtrationwas filtered
  11. washwashed with hexane
  12. customdried in vacuum tray dryer at 35° C. for 6 hrs

Sources & evidence

ORD record
ord-a6c3cf3bcf2e4bd9bd54a0e991f91f63
Source dataset
uspto-grants-2010_08
Patent number
US07772394B2

Reaction notes

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