Ethyl bromopyruvate → Ethyl 2-(cyanomethyl)-1,3-thiazole-4-carboxylate

HRID 1667850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667850
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:10]([CH2:12][C:13](=[S:15])[NH2:14])#[N:11]>CN(C)C=O>[C:10]([CH2:12][C:13]1[S:15][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:14]=1)#[N:11]

Komponenten

4

Edukt 2

HCID 66144Ethyl bromopyruvateHCID 14162772-Cyanoethanethioamide

Produkt 1

HCID 801076Ethyl 2-(cyanomethyl)-1,3-thiazole-4-carboxylateAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 3-bromo-2-oxopropanate (21 g, 110 mmol) in N,N-dimethylformamide (50 mL) was added a solution of 2-cyanoethanethioamide (10 g, 100 mmol) in N,N-dimethylformamide (50 mL) under ice-cooling, and the reaction mixture was stirred at room temperature for 12 hr. The mixture was concentrated under reduced pressure, and the obtained residue was dissolved in ethyl acetate, and washed with 5% aqueous sodium hydrogencarbonate solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→60/40) to give the title compound (5.1 g, 26%) as a yellow powder.

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe obtained residue was dissolved in ethyl acetate
  4. washwashed with 5% aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltrated
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→60/40)

Quellen und Nachweise

ORD-Eintrag
ord-5f3f3b5532a248f6b10e173c1e65715d
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044049B2

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