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

HRID 589564
Notes
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Reaction equation

HRID 589564 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 590855593-bromo-1-ethylpyrazin-2(1H)-oneYield 40.2%

Reagents, catalysts & solvents 1

HCID 6365
1,1-Dichloroethane
Solvent

Conditions

Temperature
10 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-06741394900f4961b2ae276cb4155d77
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09233937B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes