Benzyl mercaptan → 4-(benzylthio)benzonitrile

HRID 2293290Notes

Reaction equation

HRID 2293290 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 68.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 37.2 g (300 mmol) of benzylmercaptan, 36.3 g (300 mmol) 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 then with petroleum ether to give 46 g of 4-(benzylthio)benzonitrile 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

Sources & evidence

ORD record
ord-c36e402244f84ad78f65081a6d96601b
Source dataset
uspto-grants-1997_11
Patent number
US05686460

Reaction notes

Loading…