4-Chloro-2-pyridinecarbonitrile → 4-(Methylsulfanyl)pyridine-2-carbonitrile

HRID 1437240Notes

Reaction equation

HRID 1437240 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[CH:6]=1>CN(C)C=O>[CH3:1][S:2][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[CH:6]=1

Participants

4

Reactant 2

HCID 6933424-Chloro-2-pyridinecarbonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 203104474-(Methylsulfanyl)pyridine-2-carbonitrileYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium thiomethoxide (1.01 g) was added to 4-chloropyridine-2-carbonitrile (2.00 g) obtained from Referential Example 113 in N,N-dimethylformamide (20 mL) at 0° C., followed by stirring for 2 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (hexane-ethyl acetate), to thereby give the title compound as a solid (1.96 g, 90%).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  3. filtrationfollowed by filtration
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2eec23f02f314cc1b148f16b0d686b5e
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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