Tetrahydrofuran → 2-Cyano-6-methylthiopyrazine

HRID 499554Notes

Reaction equation

HRID 499554 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]#[N:9])[N:3]=1.[CH3:10][S-:11].[Na+].C1COCC1.C(OCC)(=O)C>O>[C:8]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([S:11][CH3:10])[N:3]=1)#[N:9]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 813036-Chloropyrazine-2-carbonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 229392812-Cyano-6-methylthiopyrazineYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chloro-6-cyanopyrazine (1.40 g, 10.0 mmol), sodium thiomethoxide (0.78 g, 11.0 mmol) and THF (100 ml) was refluxed for 2 hrs. The reaction mixture was combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated to give the titled compound (1.25 g, 83%) as pale yellow crystals.

Workup

  1. temperaturewas refluxed for 2 hrs
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-10c916b4118a4d4fb5af290e415fd27f
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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