Hydrochloric Acid → 6-Chloro-3-(phenylsulfanyl)-2-pyrazinecarbonitrile

HRID 392335Notes

Reaction equation

HRID 392335 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([SH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.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]([S:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 226628453,6-Dichloropyrazine-2-carbonitrile

Product 1

HCID 226628046-Chloro-3-(phenylsulfanyl)-2-pyrazinecarbonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

In 50 mL of N,N-dimethylformamide was dissolved 10.0 g of 3,6-dichloro-2-pyrazinecarbonitrile. After adding 6.49 mL of thiophenol and 11.91 g of potassium carbonate successively, the mixture thus obtained was stirred at 40° C. for 3 hours. The reaction mixture was poured into a mixture of 100 mL of ethyl acetate and 100 mL of water, and pH was adjusted to 2 with 6 mol/L hydrochloric acid. The organic layer was separated, washed successively with water and saturated aqueous solution of sodium chloride, and dried on anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent: toluene:n-hexane=1:3] to obtain 3.80 g of 6-chloro-3-(phenylsulfanyl)-2-pyrazinecarbonitrile as a light yellow-colored oily product.

Workup

  1. customthe mixture thus obtained
  2. customThe organic layer was separated
  3. washwashed 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
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography [eluent: toluene:n-hexane=1:3]

Sources & evidence

ORD record
ord-a144a20ceaec43b280990f5f7eafb94f
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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