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Potassium Carbonate → HCID 22916722, Verbindung

HRID 1376604
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1376604
[CH3:1][O:2][CH2:3][C:4]([NH:6][CH2:7][C:8]1[S:9][CH:10]=[CH:11][N:12]=1)=O.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][O:2][CH2:3][C:4]1[N:12]2[C:8]([S:9][CH:10]=[CH:11]2)=[CH:7][N:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 229166832-(Methoxyacetylamino)methylthiazole

Produkt 1

HCID 22916722HCID 22916722, VerbindungAusbeute 21,1 %

Versuchsvorschrift

To 570 mg (3.1 mmol) of the above-obtained 2-(methoxyacetylamino)methylthiazole was added 5 ml of phosphorus oxychloride. The mixture was refluxed for 4 hours, cooled to room temperature, and concentrated to dryness under reduced pressure. To the residue were added 2 ml of water and 5 ml of methylene chloride to obtain a solution, to which was added 2 g of potassium carbonate little by little. The mixture was stirred for 5 minutes. The organic layer was separated, and the aqueous layer was extracted two times with methylene chloride. The combined organic layers were dried over anhydrous potassium carbonate, concentrated under reduced pressure, and purified by flash column chromatography using silica gel, eluting with ethyl acetate. A fraction containing the desired compound was concentrated to dryness. The residue was further purified by column chromatography using Sephadex LH 20, eluting with a 1:1 mixture of chloroform and methanol to give 110 mg (yield 21%) of the title compound.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 4 hours
  2. concentrationconcentrated to dryness under reduced pressure
  3. additionTo the residue were added 2 ml of water and 5 ml of methylene chloride
  4. customto obtain a solution
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted two times with methylene chloride
  7. dry with materialThe combined organic layers were dried over anhydrous potassium carbonate
  8. concentrationconcentrated under reduced pressure
  9. custompurified by flash column chromatography
  10. washeluting with ethyl acetate
  11. additionA fraction containing the desired compound
  12. concentrationwas concentrated to dryness
  13. customThe residue was further purified by column chromatography
  14. washeluting with a 1:1 mixture of chloroform and methanol

Quellen und Nachweise

ORD-Eintrag
ord-0417985692364062bb377dbcdb24edcf
Quelldatensatz
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05663162

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