Sulfuric Acid → 2,3-Dichloro-1-oxo-1lambda~5~-pyrazine

HRID 1438862Notes

Reaction equation

HRID 1438862 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)[OH:10].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+]>>[Cl:1][C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N+:3]=1[O-:10]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24412Potassium PersulfateHCID 785752,3-Dichloropyrazine

Product 1

HCID 123755682,3-Dichloro-1-oxo-1lambda~5~-pyrazine

Procedure

To a stirred solution of 750 g. (5 mol) of 2,3-dichloropyrazine* in 5 l. of sulfuric acid at 10° C, is gradually added 1,500 g. (5.5 mol) of potassium persulfate. The reaction mixture is stirred at room temperature for 24 hours and carefully poured into 19 l. of ice water. The aqueous solution is extracted with chloroform and the extract is washed with sat. NaHCO3 and sat. NaCl solutions and dried over MgSO4. Evaporation of the solvent provides 698 g. (85%) of white solid. MP 101-103° C. (lit. MP 104°-106° C). This material is used without further purification.

Workup

  1. customat 10° C
  2. additioncarefully poured into 19 l
  3. extractionThe aqueous solution is extracted with chloroform
  4. washthe extract is washed with sat. NaHCO3 and sat. NaCl solutions
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent
  7. customprovides 698 g
  8. customThis material is used without further purification

Sources & evidence

ORD record
ord-3815f881e59943519dc63e8566df0ff0
Source dataset
uspto-grants-1977_11
Patent number
US04057517

Reaction notes

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