Ethyl bromopyruvate → Ethyl 2-(pyridin-4-YL)thiazole-4-carboxylate

HRID 278561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 278561
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[N:5]1[CH:6]=[CH:7][C:2]([C:1]2[S:8][CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:9]=2)=[CH:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 66144Ethyl bromopyruvateHCID 27237884-Pyridinecarbothioamide

Produkt 1

HCID 595483Ethyl 2-(pyridin-4-YL)thiazole-4-carboxylateAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of thioisonicotinamide (5.0 g) and ethyl bromopyruvate (7.22 g) in ethanol (90 ml) was heated for 5 hours under reflux and concentrated. To the residue were added sodium bicarbonate solution and ethyl acetate, and the organic layer was separated, washed with water and sodium chloride solution, dried and concentrated. The residue was purified with silica gel column chromatography (ethyl acetate) to give pale yellow solid of ethyl 2-(4-pyridyl)-4-thiazolecarboxylate (4.55 g).

Aufarbeitung

  1. temperatureunder reflux
  2. concentrationconcentrated
  3. additionTo the residue were added sodium bicarbonate solution and ethyl acetate
  4. customthe organic layer was separated
  5. washwashed with water and sodium chloride solution
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-940033cbb1704799b94e189e7df9d7a6
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06359134B1

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