Methanol → Ethyl 2-(pyridin-3-YL)thiazole-4-carboxylate

HRID 1174159

Reaktionsgleichung

Reaktionsgleichung von HRID 1174159
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14].CO>C(O)C.C(Cl)(Cl)Cl>[N:4]1[CH:5]=[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]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 66144Ethyl bromopyruvateHCID 737155Thionicotinamide

Produkt 1

HCID 2824169Ethyl 2-(pyridin-3-YL)thiazole-4-carboxylateAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution containing thionicotinamide (30 g, 217.1 mmol) in ethanol (540 mL) was treated with ethyl bromopyruvate (30.3 mL, 241.4 mmol), heated at 70° C. for 3 hours, cooled to 25° C., concentrated and partitioned between chloroform and saturated NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with chloroform and then with 15% methanol in chloroform containing 1% ammonium hydroxide to give the product (36.3 g, 71% yield).

Aufarbeitung

  1. temperaturecooled to 25° C.
  2. concentrationconcentrated
  3. custompartitioned between chloroform and saturated NaHCO3
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-3795f0d265e94c1dab9454718bcff6e6
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834043B2

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