Potassium Carbonate → 5-(Methylthio)-2-pyridinecarbonitrile

HRID 559823Notes

Reaction equation

HRID 559823 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH3:10][S-:11].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[CH3:10][S:11][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8171545-Bromopyridine-2-carbonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 594558745-(Methylthio)-2-pyridinecarbonitrileYield 99%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5-Bromo-pyridine-2-carbonitrile (2.63 g, 13.7 mmol), sodium methanethiolate (1.44 g, 20.5 mmol), potassium carbonate (3.79 g, 27.4 mmol) in NMP (60 ml) were stirred in a sealed flask overnight. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with water several times, brine and dried over sodium sulphate. The solvent was removed in vacuo to afford the title compound as a yellow solid (2.0 g, 99%).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with water several times, brine
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-20d66210a3aa46b0bf8d422381d632dc
Source dataset
uspto-grants-2011_11
Patent number
US08063073B2

Reaction notes

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