Water → 6-Fluoro-3,4-dihydro-3-oxo-2-pyrazinecarbonitrile

HRID 392341Notes

Reaction equation

HRID 392341 reaction equation
C([O:4][C:5]1[C:6]([C:12]#[N:13])=[N:7][C:8]([F:11])=[CH:9][N:10]=1)C=C.[Cl-].[Al+3].[Cl-].[Cl-].O>C1(C)C=CC=CC=1>[F:11][C:8]1[N:7]=[C:6]([C:12]#[N:13])[C:5](=[O:4])[NH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 226628323-(Allyloxy)-6-fluoro-2-pyrazinecarbonitrile

Product 1

HCID 226627856-Fluoro-3,4-dihydro-3-oxo-2-pyrazinecarbonitrileYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 5 mL of toluene was dissolved 1.0 g of 3-(allyloxy)-6-fluoro-2-pyrazinecarbonitrile. After adding 0.82 g of aluminum chloride, the mixture was stirred at room temperature for 1.5 hours. Water (5 mL) was added to the reaction mixture, the aqueous layer was separated, and the organic layer was extracted first with 3 mL of water and then with 2 ml of water. The aqueous layers were united and washed with 5 mL of toluene, and extracted with 15 mL of ethyl acetate. The organic layer thus obtained was washed with 3 mL of water and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Thus, 0.45 g of 6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarbonitrile was obtained as a yellow-colored solid product.

Workup

  1. customthe aqueous layer was separated
  2. extractionthe organic layer was extracted first with 3 mL of water
  3. washwashed with 5 mL of toluene
  4. extractionextracted with 15 mL of ethyl acetate
  5. customThe organic layer thus obtained
  6. washwas washed with 3 mL of water
  7. dry with materialdried on anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e71c06a78b7d47acae1587caf6a89bf6
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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