Water → 2-Phenylsulphenyl-4-trifluoromethylbenzonitrile

HRID 21455

Reaction equation

HRID 21455 reaction equation
[N+]([C:4]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.[C:16]1([SH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[C:16]1([S:22][C:4]2[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:5]=2[C:6]#[N:7])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7969Thiophenol2×HCID 11430Potassium CarbonateHCID 699022-Nitro-4-(trifluoromethyl)benzonitrile

Product 1

HCID 189779842-Phenylsulphenyl-4-trifluoromethylbenzonitrileYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-nitro-4-trifluoromethylbenzonitrile (8.64 g), thiophenol (4.4 g) and potassium carbonate (6.9 g) in acetonitrile was stirred at room temperature for 1 hour then heated at reflux for 9 hours. Thiophenol (0.3 ml) was added and the mixture was stirred and heated at reflux for 1 hour. Water was added and the mixture was extracted with dichloromethane, dried (MgSO4) and filtered. The flitrate was evaporated to dryness and the residue was recrystallized from n-hexane to give 2-(phenylsulphenyl)-4-trifluoromethylbenzonitrile (9.5 g) as a white solid, m.p. 51° C.

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 9 hours
  3. stirringthe mixture was stirred
  4. temperatureheated
  5. temperatureat reflux for 1 hour
  6. extractionthe mixture was extracted with dichloromethane
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe flitrate was evaporated to dryness
  10. customthe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-a692dcc491544bb0ae131d42e246b9a5
Source dataset
uspto-grants-1995_06
Patent number
US05424276

Linked notes

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