Thiophenol → HCID 67486222, compound

HRID 533998Notes

Reaction equation

HRID 533998 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].Br[C:12]1[CH:13]=[C:14]([N+]([O-])=O)[C:15]([C:18]#[N:19])=[N:16][CH:17]=1.[C:23]1([SH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.O>[C:23]1([S:29][C:12]2[CH:13]=[C:14]([O:8][C:7]3[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=3)[C:15]([C:18]#[N:19])=[N:16][CH:17]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 24758Sodium hydride2×HCID 707192-Methylpyridin-3-olHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

Product 1

HCID 67486222HCID 67486222, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methylpyridin-3-ol (0.96 g, 8.8 mmol) in DMF (10 mL) cooled to 0° C. was added NaH (0.35 g, 8.8 mmol) in portions and the reaction warmed to ambient temperature. To this mixture was added 5-bromo-3-nitropicolinonitrile (2.0 g, 8.8 mmol) and the reaction stirred over night at ambient temperature. To the reaction was added thiophenol (0.96 g, 8.8 mmol) and the reaction cooled to 0° C. NaH (0.35 g, 8.8 mmol) was added and the reaction warmed to ambient temperature and the reaction stirred at ambient temperature overnight. The reaction was poured into water (1000 mL) and the aqueous layer was extracted with ether (3×100 mL). The organics were washed with 1N NaOH (100 mL), water (2×100 mL) brine (100 mL), dried over MgSO4 and concentrated in vacuo to give 5-phenylthio-3-(2-methylpyridin-3-yloxy)picolinonitrile (2.8 g, 8.8 mmol, 100%) as a solid.

Workup

  1. temperaturethe reaction cooled to 0° C
  2. temperaturethe reaction warmed to ambient temperature
  3. stirringthe reaction stirred at ambient temperature overnight
  4. extractionthe aqueous layer was extracted with ether (3×100 mL)
  5. washThe organics were washed with 1N NaOH (100 mL), water (2×100 mL) brine (100 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9aecb8e4a4864e38831638c226dc109e
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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