Water → 2-Phenylsulphenyl-4-trifluoromethylbenzonitrile

HRID 2393005Notes

Reaction equation

HRID 2393005 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 7969ThiophenolHCID 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), potassium carbonate (6.9 g) in acetonitrile was heated at reflux for 4 hours. After cooling, the mixture was poured into water and extracted with dichloromethane. The organic extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The residue was triturated with hexane to give 2-phenylsulphenyl-4-trifluoromethylbenzonitrile as a white solid (9.5 g), m.p. 51° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureAfter cooling
  4. extractionextracted with dichloromethane
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-3bef2b92771c4c74a2da6161afe08d5c
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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