Ethyl Acetate → 6-Chloro-3-(4-methoxyphenoxy)-2-pyrazinecarbonitrile

HRID 392332Notes

Reaction equation

HRID 392332 reaction equation
Cl[C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([Cl:8])=[CH:6][N:7]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[Cl:8][C:5]1[N:4]=[C:3]([C:9]#[N:10])[C:2]([O:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[N:7][CH:6]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 226628453,6-Dichloropyrazine-2-carbonitrile

Product 1

HCID 226628486-Chloro-3-(4-methoxyphenoxy)-2-pyrazinecarbonitrileYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 15 ml of dimethylformamide was dissolved 1.5 g of 3,6-dichloro-2-pyrazinecarbonitrile. After adding 1.2 g of 4-methoxyphenol and 1.8 g of potassium carbonate, the mixture thus obtained was stirred at room temperature for 30 minutes. A mixture of 20 mL of ethyl acetate and 60 mL of water was added to the reaction mixture, and the organic layer was separated. The organic layer was washed successively with water and 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 column chromatography [eluent: n-hexane:ethyl acetate=5:1] to obtain 2.1 g of 6-chloro-3-(4-methoxyphenoxy)-2-pyrazinecarbonitrile as a yellow-colored solid product.

Workup

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

Sources & evidence

ORD record
ord-7a00c41b2fdd4786ab99c6fb249a06bf
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

Loading…