Potassium Iodide → HCID 21931845, Verbindung

HRID 1243990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243990
[I-].[K+].[Cl-].[CH3:4][S+](C)(C)=O.[H-].[Na+].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH3:23])[C:18](=[O:24])[CH:17]=[CH:16]2>CS(C)=O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20]([N:19]([CH3:23])[C:18](=[O:24])[CH:17]3[CH2:4][CH:16]32)=[CH:21][CH:22]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 197819Trimethyloxosulphonium chlorideHCID 2204596-Methoxy-1-methyl-2(1H)-quinolinone

Produkt 1

HCID 21931845HCID 21931845, VerbindungAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A suspension of 7.0 gm (42.0 mmol) potassium iodide and 4.89 gm (38.0 mmol) trimethylsulfoxonium chloride in 30 ml of DMSO under nitrogen was treated portionwise with 1.69 gm (42.0 mmol) of 60% sodium hydride in mineral oil. The mixture was stirred for one hour and then treated with 2.0 gm (11.0 mmol) 6-Methoxy-1-methyl-1H-quinolin-2-one followed by stirring for 0.5 hours at ambient temperature and 4 days at 90° C. The reaction mixture was allowed to cool to ambient temperature before quenching into ice followed by extraction into ether. The ether layer was washed with brine, dried over sodium sulfate and evaporated. The residue was partitioned between acetonitrile and pentane. The acetonitrile layer was concentrated. The residue was partitioned between 1:1 hexane/ethyl acetate and 50% saturated (sat'd) brine solution. The organic layer was washed with saturated brine, dried over sodium sulfate and evaporated in vacuo to afford 1.6 gm of a mixture of desired product and starting material. The residue was purified by silica gel chromatography eluting with 7/3 hexane/ethyl acetate to afford 972 mg (44%). Mass spectrum APCI m/e 204 (p+1).

Aufarbeitung

  1. stirringby stirring for 0.5 hours at ambient temperature and 4 days at 90° C
  2. custombefore quenching into ice
  3. extractionfollowed by extraction into ether
  4. washThe ether layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was partitioned between acetonitrile and pentane
  8. concentrationThe acetonitrile layer was concentrated
  9. customThe residue was partitioned between 1:1 hexane/ethyl acetate and 50% saturated (sat'd) brine solution
  10. washThe organic layer was washed with saturated brine
  11. dry with materialdried over sodium sulfate
  12. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-745c01c24eec470eb1e4bfee29f6670b
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119207B2

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