Thiophenol → 2-Chloro-6-(phenylsulfanyl)pyrazine

HRID 1679659Notes

Reaction equation

HRID 1679659 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[H-].[Na+]>CN(C)C=O>[C:9]1([S:15][C:2]2[N:3]=[C:4]([Cl:8])[CH:5]=[N:6][CH:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 785042,6-Dichloropyrazine

Product 1

HCID 203616992-Chloro-6-(phenylsulfanyl)pyrazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,6-dichloropyrazine (0.100 mol) and freshly distilled thiophenol (0.100 mol) in 200 ml. N,N-dimethylformamide is treated with five grams of sodium hydride (50% dispersion in Nujol) gradually with vigorous stirring under nitrogen at room temperature. After 3 hr. the mixture is concentrated in vacuo, and the residue partitioned between water and benzene. The benzene extract is washed with water, dried (anhydrous sodium sulfate), and concentrated in vacuo to an oil which is the crude title compound.

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. customthe residue partitioned between water and benzene
  3. extractionThe benzene extract
  4. washis washed with water
  5. dry with materialdried (anhydrous sodium sulfate)
  6. concentrationconcentrated in vacuo to an oil which

Sources & evidence

ORD record
ord-9f7ef5f419e54624bb2afdbc4c4ea6e2
Source dataset
uspto-grants-1978_03
Patent number
US04081542

Reaction notes

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