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Water → 3-bromo-1-ethylpyrazin-2(1H)-one

HRID 512105
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 512105
[CH2:1]([N:3]1[CH:8]=[CH:7][N:6]=[C:5](O)[C:4]1=[O:10])[CH3:2].P(Br)(Br)([Br:13])=O.C(=O)([O-])[O-].[Na+].[Na+].O>ClC(Cl)C>[Br:13][C:5]1[C:4](=[O:10])[N:3]([CH2:1][CH3:2])[CH:8]=[CH:7][N:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24613Phosphorus oxybromideHCID 178462754HCID 178462754, Verbindung

Produkt 1

HCID 590855593-bromo-1-ethylpyrazin-2(1H)-oneAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6365
1,1-Dichloroethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

10.5 g (75 mM) of 1-ethyl-3-hydroxypyrazine-2(1H)-one and 23.1 g (80.5 mM) of phosphorous oxybromide in 75 ml of dichloroethane were refluxed under stirring for 2 h. The reaction mixture was then neutralized to pH 7-8 with a saturated aqueous solution of sodium carbonate, while maintaining the temperature at 10° C. The reaction mixture was then stirred at room temperature for 1 h. Water was added and the organic phase was extracted with dichloromethane. The combined organic layer was washed with water, dried on anhydrous sodium sulfate and the solvent was removed under vacuum. The compound was further purified by silica gel column chromatography, using dichloromethane as eluant, to give 6.1 g of 3-bromo-1-ethylpyrazin-2(1H)-one as a solid. Yield: 40.2%.

Aufarbeitung

  1. stirringThe reaction mixture was then stirred at room temperature for 1 h
  2. extractionthe organic phase was extracted with dichloromethane
  3. washThe combined organic layer was washed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customthe solvent was removed under vacuum
  6. customThe compound was further purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b5fd655250f5454481debcbee3b2a094
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09102632B2

Notizen zur Reaktion

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