Water → 2-(1-Methylpropylsulphenyl)-4-trifluoromethylbenzonitrile

HRID 2393032Notes

Reaction equation

HRID 2393032 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.[CH3:16][CH:17]([SH:20])[CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:16][CH:17]([S:20][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])[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 105602-ButanethiolHCID 11430Potassium CarbonateHCID 699022-Nitro-4-(trifluoromethyl)benzonitrile

Product 1

HCID 543393872-(1-Methylpropylsulphenyl)-4-trifluoromethylbenzonitrileYield 86.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-nitro-4-trifluoromethylbenzonitrile (10.8 g), 1-methyl-1-propanethiol (7.5 g) and potassium carbonate (8.3 g) in acetonitrile was stirred and heated at reflux for 8 hours. It was cooled, water was added and the layers were separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water, dried (magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography eluted with a mixture of ethyl acetate and cyclohexane to give 2-(1-methylpropylsulphenyl)-4-trifluoromethylbenzonitrile (11.2 g) as a yellow oil NMR (CDCl3); 1.0(t,3H), 1.35(d,3H), 1.7(m,2H), 3.45(m,1H), 7.5(d,1H), 7.7(s,1H), 7.75(d,1H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 8 hours
  3. temperatureIt was cooled
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washthe combined organic layers were washed with water
  7. dry with materialdried (magnesium sulphate)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. customthe residue was purified by chromatography
  11. washeluted with a mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-fc521003e0674905bdfab5806ff36d41
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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