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

HRID 499568Notes

Reaction equation

HRID 499568 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-18dfba0e4c7c4f1aa9526e630f8c7848
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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