3-Chloropyridine-2-carbonitrile → 3-Sulfanylpyridine-2-carbonitrile
Reaction equation
Cl[C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C[S-:11].[Na+]>CN1CCCC1=O>[SH:11][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A mixture of 3-chloro-2-cyanopyridine (2.50 g, 18.05 mmol), and sodium thiomethoxide (3.60 g, 51.40 mmol) in 1-methyl-2-pyrrolidinone (25 mL) was heated at 140° C. overnight. The reaction mixture was cooled to 0° C. and quenched with 50% aqueous HCl. A light brown precipitate formed and the reaction was cooled for 1 h while stirring. The light brown solid was collected by vacuum filtration and dried under reduced pressure overnight to provide 3-mercaptopicolinonitrile (1.05 g). The crude product was used carried forward without further purification. MW=136 confirmed by LC-MS, tr=1.85 min (Method E) MH+=137.
Workup
- temperatureThe reaction mixture was cooled to 0° C.
- customquenched with 50% aqueous HCl
- customA light brown precipitate formed
- temperaturethe reaction was cooled for 1 h
- filtrationThe light brown solid was collected by vacuum filtration
- customdried under reduced pressure overnight
Sources & evidence
- ORD record
- ord-077c922f2e7d4a9493291f7af4a6031e
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776847B2
Reaction notes
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