Methyl iodide → 6-Chloro-3-(4-methoxyphenoxy)-2-pyrazinecarbonitrile

HRID 392334Notes

Reaction equation

HRID 392334 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[N:4][CH:3]=1.IC.[C:20](=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:20])=[CH:13][CH:12]=2)=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 226627696-Chloro-3-(4-hydroxyphenoxy)-2-pyrazinecarbonitrile

Product 1

HCID 226628486-Chloro-3-(4-methoxyphenoxy)-2-pyrazinecarbonitrileYield 101.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 8 mL of dimethylformamide was dissolved 0.4 g of 6-chloro-3-(4-hydroxyphenoxy)-2-pyrazinecarbonitrile. After adding 0.5 ml of iodomethane and 0.89 g of potassium carbonate, the mixture thus obtained was stirred at room temperature for 30 minutes. The reaction mixture was added to a mixture of 10 mL of ethyl acetate and 30 mL of water, 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. Thus, 0.43 g of 6-chloro-3-(4-methoxyphenoxy)-2-pyrazinecarbonitrile was obtained as a yellow-brown colored solid product.

Workup

  1. customthe mixture thus obtained
  2. customthe organic layer was separated
  3. washThe organic layer was washed successively with water and 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-d77dcb9fa0ed4b6d8870503764a58ad8
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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