Tetrahydrofuran → 6-(Methylsulfanyl)pyridine-3-carbonitrile

HRID 499418Notes

Reaction equation

HRID 499418 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.[CH3:10][S-:11].[Na+].C1COCC1.C(OCC)(=O)C>O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([S:11][CH3:10])=[N:3][CH:4]=1)#[N:9]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 4378561Sodium methanethiolateHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 229395276-(Methylsulfanyl)pyridine-3-carbonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloro-5-cyanopyridine (2.10 g, 15.1 mmol) and sodium thiomethoxide (1.16 g, 16.5 mmol) were added to THF (30 ml). The reaction mixture was refluxed for 9 hrs and 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 (2.26 g, 100%) as pale yellow crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 9 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-87a4d9ad0796450d925b4650bea98971
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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