Benzyl mercaptan → 6-(Benzylthio)picolinonitrile

HRID 499409Notes

Reaction equation

HRID 499409 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[N:13]=1.C(OCC)(=O)C>C1COCC1.[Cl-].[Na+].O>[CH2:1]([S:8][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 1184246-Chloropyridine-2-carbonitrile

Product 1

HCID 229396226-(Benzylthio)picolinonitrileYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Benzyl mercaptan (0.99 g, 7.94 mmol) and sodium hydride (60% in oil, 0.35 g, 8.66 mmol) were added to THF (30 ml), and the mixture was stirred at room temperature for 1 hr. A solution of 2-chloro-6-cyanopyridine (1.00 g, 7.22 mmol) in THF (10 ml) was added dropwise to the reaction mixture, and the mixture was stirred at room temperature for 18 hrs. The reaction mixture was combined with ethyl acetate and brine. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the titled compound (1.63 g, 100%) as a pale pink oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hrs
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0f0c4c413ca14df98cec5b11f94676a2
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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