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

HRID 1728921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1728921
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 152250344-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-5-acetonitrileAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c3a7215459c6468fa80c4fe1aeae4247
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05329016

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