Benzyl mercaptan → 4-(benzylthio)benzonitrile

HRID 568075Notes

Reaction equation

HRID 568075 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([S:8][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

Product 1

HCID 8525724-(benzylthio)benzonitrileYield 68.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 37.2 g of benzylmercaptan, 36.3 g of 4-fluorobenzonitrile and 42 g of potassium carbonate in 700 ml of 2-butanone is refluxed for 7 hours. The solvent is evaporated off under vacuum and the residue is taken up with water and petroleum ether. The crystals formed are filtered off and washed with water and petroleum ether to give 46 g of 4-benzylthiobenzonitrile in the form of crystals melting at 85° C.

Workup

  1. temperatureis refluxed for 7 hours
  2. customThe solvent is evaporated off under vacuum
  3. customThe crystals formed
  4. filtrationare filtered off
  5. washwashed with water and petroleum ether

Sources & evidence

ORD record
ord-269dd2131b3844b49f00974509f2987d
Source dataset
uspto-grants-2001_01
Patent number
US06180651B2

Reaction notes

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