Hydrochloric Acid → 6-Fluoro-3,4-dihydro-3-oxo-2-pyrazinecarbonitrile

HRID 392339Notes

Reaction equation

HRID 392339 reaction equation
F[C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([F:8])=[CH:6][N:7]=1.C([O-])(=[O:13])C.[Na+].C(OCC)(=O)C.Cl>CN(C)C=O.O>[F:8][C:5]1[N:4]=[C:3]([C:9]#[N:10])[C:2](=[O:13])[NH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 226628293,6-Difluoropyrazine-2-carbonitrile

Product 1

HCID 226627856-Fluoro-3,4-dihydro-3-oxo-2-pyrazinecarbonitrileYield 45.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 10 mL of N,N-dimethylformamide was dissolved 1.0 g of 3,6-difluoro-2-pyrazinecarbonitrile. At an ice-cooled temperature, 0.64 g of sodium acetate was added and stirred for 6 hours. The reaction mixture was added to a mixture of 20 mL of ethyl acetate and 20 mL of water, pH was adjusted to 1.5 with 6 mol/L hydrochloric acid, and the organic layer was separated. The organic layer was washed with saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel chromatography [eluent: n-hexane:ethyl acetate-: 1:1] to obtain 0.45 g of 6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarbonitrile as a yellow-colored solid product.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried on anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel chromatography [eluent: n-hexane:ethyl acetate-: 1:1]

Sources & evidence

ORD record
ord-203f600d50494698b4ee57f06964d1dd
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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