Acetic Acid → 2-Isopropylthio-3-(cyclohexanon-2-yloxy)-pyridine

HRID 55550

Reaktionsgleichung

Reaktionsgleichung von HRID 55550
Cl[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[CH:9]([S:12][C:13]1[C:18]([OH:19])=[CH:17][CH:16]=[CH:15][N:14]=1)([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CN(C)C=O.C(OCC)(=O)C>[CH:9]([S:12][C:13]1[C:18]([O:19][CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2=[O:8])=[CH:17][CH:16]=[CH:15][N:14]=1)([CH3:11])[CH3:10]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 11430Potassium Carbonate3×HCID 132032-Chlorocyclohexanone3×HCID 199579323-Pyridinol, 2-[(1-methylethyl)thio]-

Produkt 1

HCID 570183552-Isopropylthio-3-(cyclohexanon-2-yloxy)-pyridineAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

7.29 g of 2-chlorocyclohexanone are added at room temperature to a mixture of 8.4 g of 2-isopropylthio-3-hydroxypyridine and 7.6 g of potassium carbonate in 120 ml of dimethylformamide, and the mixture is stirred for one hour at 45°-50° C. After the addition of 1.46 g of 2-chlorocyclohexanone and 1.52 g of potassium carbonate and after 2 hours of a further analogous addition of 0.73 g of 2-chlorocyclohexanone and 0.76 g of potassium carbonate, the suspension is stirred for a further 3.5 hours at 45°-50° C. The resulting reaction solution is poured onto a mixture consisting of 200 ml of ice-water, 50 ml of 2N acetic acid and 100 ml of ethyl acetate, washed three times with 300 ml of ethyl acetate and 100 ml of saturated sodium chloride solution each time, dried over sodium sulfate and concentrated by evaporation. The residue is triturated with petroleum ether and filtered. 9.57 g of the desired ketone having a melting point of 106°-110° C. are obtained.

Aufarbeitung

  1. stirringthe suspension is stirred for a further 3.5 hours at 45°-50° C
  2. customThe resulting reaction solution
  3. additionis poured onto a mixture
  4. washwashed three times with 300 ml of ethyl acetate and 100 ml of saturated sodium chloride solution each time
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customThe residue is triturated with petroleum ether
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-917b3d08128a40d7a7314a146b67dcc5
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05625071

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