Sodium Chloride → Ethyl (1,3-thiazol-2-yl)acetate

HRID 218231

Reaktionsgleichung

Reaktionsgleichung von HRID 218231
[S:1]1[CH:5]=[CH:4][NH:3][C:2]1=[C:6](C(OCC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl-].[Na+]>CS(C)=O.O>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Komponenten

5

Edukt 2

HCID 5234Sodium ChlorideHCID 10977652Diethyl 2-(thiazol-2(3H)-ylidene)malonate

Produkt 1

HCID 21835228Ethyl (1,3-thiazol-2-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of the product of Example 44B (2.8 g, 11.5 mmoles), sodium chloride (1.3 g, 22.9 mmoles) and water (0.4 ml, 22.9 mmoles) in dimethyl sulfoxide (48.0 ml) was stirred at about 180° C. for about 30 min. The mixture was cooled, diluted with water (100.0 ml) and was extracted twice with (1:1) ethyl acetate/diethyl ether (80.0 ml each). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuum. The crude product was purified by flash column chromatography on silica gel using hexanes/ethyl acetate (2:1) as the mobile phase to provide the title compound.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionwas extracted twice with (1:1) ethyl acetate/diethyl ether (80.0 ml each)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe crude product was purified by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ae3ff4bad61642ed90f38fc3b7507639
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198331B2

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