Dimethylformamide → 3-(Ethylthio)picolinonitrile

HRID 713653Notes

Reaction equation

HRID 713653 reaction equation
[CH2:1]([SH:3])[CH3:2].Cl[C:5]1[C:6]([C:11]#[N:12])=[N:7][CH:8]=[CH:9][CH:10]=1.CN(C=O)C.[H-].[Na+]>O>[CH2:1]([S:3][C:5]1[C:6]([C:11]#[N:12])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 8182583-Chloropyridine-2-carbonitrile

Product 1

HCID 224645153-(Ethylthio)picolinonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.9 mL of ethanethiol was added to a mixture of 1.39 g of 3-chloropyridine-2-carbonitrile and 10 mL of DMF, 0.52 g of 60% sodium hydride (oil-based) was added to the reaction mixture under ice cooling, and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured to water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 1.52 g of 3-ethylsulfanylpyridine-2-carbonitrile.

Workup

  1. additionwas added to the reaction mixture under ice cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dcc6c9eabd1f46efa58246245ee1771b
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

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