Hydrochloric Acid → 6-Chloro-3-(4-hydroxyphenoxy)-2-pyrazinecarbonitrile

HRID 392331Notes

Reaction equation

HRID 392331 reaction equation
Cl[C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([Cl:8])=[CH:6][N:7]=1.[C:11]1([CH:18]=[CH:17][C:15]([OH:16])=[CH:14][CH:13]=1)[OH:12].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O.C(OCC)(=O)C>[Cl:8][C:5]1[N:4]=[C:3]([C:9]#[N:10])[C:2]([O:12][C:11]2[CH:18]=[CH:17][C:15]([OH:16])=[CH:14][CH:13]=2)=[N:7][CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 226628453,6-Dichloropyrazine-2-carbonitrile

Product 1

HCID 226627696-Chloro-3-(4-hydroxyphenoxy)-2-pyrazinecarbonitrileYield 70.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 10 mL of dimethylformamide was dissolved 1.0 g of 3,6-dichloro-2-pyrazinecarbonitrile. After adding 0.7 g of hydroquinone and 1.74 g of potassium carbonate, the mixture thus obtained was stirred at room temperature for 30 minutes. The reaction mixture was poured into a mixture of 10 mL of ethyl acetate and 30 mL of water, pH was adjusted to 7 with 2 mol/L hydrochloric acid, and the organic layer was separated. The organic layer thus obtained 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 was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=3:1] to obtain 1.0 g of 6-chloro-3-(4-hydroxyphenoxy)-2-pyrazinecarbonitrile as a yellow-colored solid product.

Workup

  1. customthe mixture thus obtained
  2. customthe organic layer was separated
  3. customThe organic layer thus obtained
  4. washwas 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 was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=3:1]

Sources & evidence

ORD record
ord-974bc07f7843422699d908abdc4765b6
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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