Water → HCID 59085559, compound

HRID 512105Notes

Reaction equation

HRID 512105 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

Participants

6

Reactant 4

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

Product 1

HCID 59085559HCID 59085559, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

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. Yield: 40.2%.

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-b5fd655250f5454481debcbee3b2a094
Source dataset
uspto-grants-2015_08
Patent number
US09102632B2

Reaction notes

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