Chloroacetic Acid → 1(2H)-Pyrazineacetic acid, 2-oxo-

HRID 1888178

Reaktionsgleichung

Reaktionsgleichung von HRID 1888178
[NH:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]1=[O:7].[OH-].[Na+].Cl[CH2:11][C:12]([OH:14])=[O:13].Cl>>[O:7]=[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]1[CH2:11][C:12]([OH:14])=[O:13]

Komponenten

5

Edukt 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 727581,2-Dihydropyrazin-2-one

Produkt 1

HCID 217140981(2H)-Pyrazineacetic acid, 2-oxo-

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To Pyrazin-2(1H)-one (0.333 g, 3.47 mmol) was added 5 N sodium hydroxide solution (2.1 ml) followed by chloroacetic acid (0.524 g, 5.54 mmol). The reaction mixture was heated at 100° C. for 2 h. After cooling to ambient temperature, 2 N hydrochloric acid (3.5 ml) was added and the reaction mixture was directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). The pure fractions were lyophilized overnight to yield the title compound as a yellow solid. LC/MS 155.2 (M+1)+.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customthe reaction mixture was directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient)

Quellen und Nachweise

ORD-Eintrag
ord-3638307d96834b78aa45ca088bb644e8
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501786B2

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