Thionyl Chloride → 3,5-Dichloro-6-ethylpyrazine-2-carbonitrile

HRID 869219Notes

Reaction equation

HRID 869219 reaction equation
[Cl:1][C:2]1[C:3]([C:11]([NH2:13])=O)=[N:4][C:5]([CH2:9][CH3:10])=[C:6]([Cl:8])[N:7]=1.S(Cl)(Cl)=O>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:11]#[N:13])=[N:4][C:5]([CH2:9][CH3:10])=[C:6]([Cl:8])[N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 848199603,5-Dichloro-6-ethylpyrazine-2-carboxamide

Product 1

HCID 848198773,5-Dichloro-6-ethylpyrazine-2-carbonitrileYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (1.0 g) and DMF (15 mL), thionyl chloride (1 mL) was added at room temperature and stirred for 20 minutes. The reaction liquid was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane) to give 3,5-dichloro-6-ethylpyrazine-2-carbonitrile (608 mg) as a slightly yellow oil.

Workup

  1. additionwas added at room temperature
  2. customThe reaction liquid
  3. additionwas poured into ice-cold water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane)

Sources & evidence

ORD record
ord-0c7ad0b29e07437d8b38309a8e37f469
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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