3-Chlorothiophenol → 3-[[(3-Chlorophenyl)thio]methyl]-2-pyridinecarbonitrile

HRID 1647249Notes

Reaction equation

HRID 1647249 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:6]=[C:7]([SH:11])[CH:8]=[CH:9][CH:10]=1.[C:12]([C:14]1[C:19]([CH2:20]Br)=[CH:18][CH:17]=[CH:16][N:15]=1)#[N:13]>CO>[C:12]([C:14]1[C:19]([CH2:20][S:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([Cl:4])[CH:6]=2)=[CH:18][CH:17]=[CH:16][N:15]=1)#[N:13]

Participants

5

Reactant 3

HCID 162573-ChlorothiophenolHCID 103754503-(Bromomethyl)pyridine-2-carbonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 152802283-[[(3-Chlorophenyl)thio]methyl]-2-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a stirred, cloudy solution of sodium methoxide (14.7 g, 0.27 mol) in methanol (450 mL), contained in a water bath, add a solution of 3-chlorothiophenol (39.5 g, 0.27 mol) in methanol (95 mL). To the resultant solution add a solution of 2-cyano-3-(bromomethyl)pyridine (48.9 g, 0.25 mol) in methanol (195 mL), and stir the reaction mixture at room temperature for 1 h. Concentrate the reaction mixture under reduced pressure, add 500 mL of ether to the residue, stir, and filter to remove the sodium bromide. Evaporate ether under reduced pressure to obtain the title compound as an amber oil, which may be used without further purification.

Workup

  1. concentrationConcentrate the reaction mixture under reduced pressure
  2. additionadd 500 mL of ether to the residue
  3. stirringstir
  4. filtrationfilter
  5. customto remove the sodium bromide

Sources & evidence

ORD record
ord-eccfa7eb6d1249b5856b54ee2c4c26cc
Source dataset
uspto-grants-1995_07
Patent number
US05430032

Reaction notes

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