Water → 3-Azido-6-fluoro-2-pyrazinecarbonitrile

HRID 392345Notes

Reaction equation

HRID 392345 reaction equation
F[C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([F:8])=[CH:6][N:7]=1.[N-:11]=[N+:12]=[N-:13].[Na+].CCOCC.O>CN(C)C=O>[N:11]([C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([F:8])=[CH:6][N:7]=1)=[N+:12]=[N-:13]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 33557Sodium AzideHCID 226628293,6-Difluoropyrazine-2-carbonitrile

Product 1

HCID 226627893-Azido-6-fluoro-2-pyrazinecarbonitrileYield 107.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 2.0 mL of N,N-dimethylformamide was dissolved 0.20 g of 3,6-difluoro-2-pyrazinecarbonitrile. At 5° C., 0.11 g of sodium azide was added and stirred at the same temperature as above for 10 minutes. The reaction mixture was added to a mixture of 20 mL of ether and 20 mL of water, and the organic layer was separated. The organic layer thus obtained was washed successively with 20 mL of water and 20 mL of saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Thus, 0.25 g of 3-azido-6-fluoro-2-pyrazinecarbonitrile was obtained as a yellow-colored oily product.

Workup

  1. customthe organic layer was separated
  2. customThe organic layer thus obtained
  3. washwas washed successively with 20 mL of water and 20 mL of saturated aqueous solution of sodium chloride
  4. dry with materialdried on anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-97a9423331194902967e668727bee64f
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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