Sulfuric acid magnesium salt (1:1) → Ethyl 2-(morpholin-4-yl)-1,3-thiazole-4-carboxylate

HRID 443122Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 443122
[NH2:1][C:2]([N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)=[S:3].Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14].[O-]S([O-])(=O)=O.[Mg+2]>CC(C)=O>[N:4]1([C:2]2[S:3][CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:1]=2)[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1

Komponenten

5

Edukt 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 66144Ethyl bromopyruvateHCID 23935444-Morpholinecarbothioamide

Produkt 1

HCID 15053544Ethyl 2-(morpholin-4-yl)-1,3-thiazole-4-carboxylateAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 1.85 g (12.7 mmol) of 4-((amino)thiocarbonyl)morpholine, 1.59 ml (12.7 mmol) of ethyl bromopyruvate, and excess MgSO4 in 50 ml of acetone was heated at reflux for 2 h. The resulting mixture was allowed to cool, filtered, and concentrated in vacuo. The residue was taken up in chloroform, washed with aqueous NaHCO3, dried over Na2SO4, and concentrated. Silica gel chromatography using 1% methanol in chloroform provided 1.7 g (55%) of the desired compound, Rf 0.70 (ethyl acetate). Mass spectrum: (M+H)+ =243.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washwashed with aqueous NaHCO3
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-90b941ba99434f869fd82e6e691a9dc7
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05892052

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