Sodium hydride → 2-Sulfanylpyridine-3-carbonitrile

HRID 502588Notes

Reaction equation

HRID 502588 reaction equation
[C:1]([C:3]1[C:4]([S:9]CCC(OC)=O)=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+]>O1CCCC1>[S:9]=[C:4]1[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][NH:5]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 13793439Methyl 3-(3-cyanopyridin-2-ylthio)propanoate

Product 1

HCID 43864192-Sulfanylpyridine-3-carbonitrileYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-(3-cyanopyridin-2-ylthio)propanoate (1.5 g, 6.8 mmol), sodium hydride (0.36 g, 15 mmol) and tetrahydrofuran (30 ml) was heated at reflux for 5 h. The reaction was quenched by the addition of ethanol (5 ml). The solvents removed under reduced pressure and the residue was treated with water (50 ml). The ph was adjusted to 6 and the mixture was filtered to yield 2-thioxo-1,2-dihydropyridine-3-carbonitrile (0.64 g). An analytically pure sample was prepared by recrystallisation from ethanol, yellow needles, mp 243-246° C. (lit. mp 248-250° C.). 1H NMR (DMSO-d6): 14.30 (br s, exchangeable, 1H), 8.12 (dd, 1H), 7.94 (dd, 1H), 6.86 ppm (dd, 1H). MW=136 confirmed by LC-MS, tr=5.27 min (Method C) MH+=137.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. customThe reaction was quenched by the addition of ethanol (5 ml)
  4. customThe solvents removed under reduced pressure
  5. additionthe residue was treated with water (50 ml)
  6. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-ef715c14598b42b18799208d3e7902e0
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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