6-Chloropyridine-2-carbonitrile → HCID 22939445, compound

HRID 748112Notes

Reaction equation

HRID 748112 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[N:9])[N:3]=1.[CH3:10][S-:11].[Na+]>O1CCCC1>[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([S:11][CH3:10])[N:3]=1)#[N:9]

Participants

4

Reactant 2

HCID 1184246-Chloropyridine-2-carbonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 22939445HCID 22939445, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-chloro-6-cyanopyridine (0.70 g, 5.0 mmol), sodium thiomethoxide (0.39 g, 5.5 mmol) and tetrahydrofuran (50 ml) was stirred at 90° C. for 18 hrs. The reaction mixture was concentrated under reduced pressure, combined with water and extracted with ethyl acetate. The extract was washed with saturated brine and dried, and the solvent was evaporated under reduced pressure to give the titled compound as an oil (0.76 g, 98%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-386feda9668d4b26ae65113fde6ce181
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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