Water → 4-(Methylsulfanyl)pyridine-2-carbonitrile

HRID 748387Notes

Reaction equation

HRID 748387 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1.[CH3:10][S-:11].[Na+].C(OCC)(=O)C.O>C1COCC1>[C:8]([C:4]1[CH:3]=[C:2]([S:11][CH3:10])[CH:7]=[CH:6][N:5]=1)#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 6933424-Chloro-2-pyridinecarbonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 203104474-(Methylsulfanyl)pyridine-2-carbonitrileYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-2-cyanopyridine (2.18 g, 15.7 mmol) and sodium thiomethoxide (2.20 g, 31.4 mmol) were dissolved in THF (100 ml), and the mixture 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 anhydrous magnesium sulfate. The solvent was evaporated to give the titled compound (2.36 g, 99%) as pale yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-4a88848a7ff94732ba922676210f4ffe
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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