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

HRID 266588Notes

Reaction equation

HRID 266588 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(=O)([O-])[O-].[K+].[K+].[CH3:22][CH:23]([SH:26])[CH2:24][CH3:25].O>C(#N)C>[CH3:22][CH:23]([S:26][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])[CH2:24][CH3:25]

Participants

6

Reactant 4

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

Product 1

HCID 543393872-(1-Methylpropylsulphenyl)-4-trifluoromethylbenzonitrileYield 74.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-Nitro-4-trifluoromethylbenzonitrile (10.8 g) and potassium carbonate (8.3 g) were heated to reflux in acetonitrile. A solution of 1-methylpropanethiol (5 g) in acetonitrile was added. The resultant suspension was heated at reflux for 4.5 hours. After cooling water was added and the mixture extracted with ethyl acetate. The organic extracts were washed with water. The organic extracts were washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue purified by column chromatography eluting with ethyl acetate in cyclohexane to give 2-(1-methylpropylsulphenyl)-4-trifluoromethylbenzonitrile (9.7 g) as a yellow oil, NMR (CDCl3) 1.0(t,3H), 1.2(d,3H), 1.5(m,2H), 3.4(m, 1H), 7.3(m, 1H), 7.6(m,2H).

Workup

  1. temperatureat reflux for 4.5 hours
  2. additionwas added
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe organic extracts were washed with water
  5. washThe organic extracts were washed with water
  6. dry with materialdried (anhydrous magnesium sulphate)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue purified by column chromatography
  10. washeluting with ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-fcd1f0af46364d8fb7a6f425dab26908
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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