Methanol → 4-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-5-acetonitrile

HRID 1681822Notes

Reaction equation

HRID 1681822 reaction equation
[C-:1]#[N:2].[K+].CO.Cl.CN([CH2:10][CH:11]1[CH2:16][S:15][C:14]2[S:17][CH:18]=[CH:19][C:13]=2[C:12]1=[O:20])C>O>[O:20]=[C:12]1[CH:11]([CH2:10][C:1]#[N:2])[CH2:16][S:15][C:14]2[S:17][CH:18]=[CH:19][C:13]1=2

Participants

5

Reactant 3

HCID 887MethanolHCID 9032Potassium CyanideHCID 126753075-dimethylaminomethyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one hydrochloride

Product 1

HCID 152250344-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-5-acetonitrileYield 86.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 25.3 g of potassium cyanide in 100 ml of water is added 400 ml of methanol and to the solution is added 41 g of 5-dimethylaminomethyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one hydrochloride with stirring. The mixture is stirred for 3 hours at 45°-50° C. and then concentrated under reduced pressure. To the residue is added water and the mixture is extracted with chloroform. The extract is washed with water, dried over magnesium sulfate and the chloroform is distilled off. The residue is subjected to chromatography on silica gel and eluted with chloroform to give 28 g of 4-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-5-acetonitrile as pale brown oil.

Workup

  1. stirringThe mixture is stirred for 3 hours at 45°-50° C.
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue is added water
  4. extractionthe mixture is extracted with chloroform
  5. washThe extract is washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationthe chloroform is distilled off
  8. washeluted with chloroform

Sources & evidence

ORD record
ord-626ca19696b145eab97393b43addbe27
Source dataset
uspto-grants-1992_12
Patent number
US05175162

Reaction notes

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