Allyl Alcohol → HCID 20482369, compound

HRID 648183Notes

Reaction equation

HRID 648183 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH:4]=[CH2:5].[H][H].Br[C:10]1[S:11][C:12]([C:15](=[O:19])[N:16]([CH3:18])[CH3:17])=[CH:13][N:14]=1>CN(C)C=O.O>[CH2:3]([O:6][C:10]1[S:11][C:12]([C:15](=[O:19])[N:16]([CH3:18])[CH3:17])=[CH:13][N:14]=1)[CH:4]=[CH2:5]

Participants

7

Reactant 4

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 2048236887807-88-3HCID 178418361HCID 178418361, compound

Product 1

HCID 20482369HCID 20482369, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 0.5 g (10 mmol) of sodium hydride in 5 ml of dry N,N-di-methylformamide under N2, there can be added 0.6 g (10 mmol) of sieve-dried allyl alcohol. After hydrogen evolution ceases, the stirred solution can be treated with 2-bromo-5-(N,N-dimethylcarbamoyl)thiazole (2.35 g, 10.0 mmole). The mixture can then be stirred at 40° under N2 for 18 hours, diluted with four volumes of water and extracted with ether. The ether extracts can be washed with water, dried (Na2SO4), filtered and concentrated in vacuo to give an oil which can then be distilled to give pure title compound.

Workup

  1. extractionextracted with ether
  2. washThe ether extracts can be washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an oil which
  7. distillationcan then be distilled

Sources & evidence

ORD record
ord-fe7237d345e04ac1b1577aef2ef9156c
Source dataset
uspto-grants-1983_10
Patent number
US04411899

Reaction notes

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