2-Aminothiophenol → Amino-2-[2-(4-cyanophenyl)ethylthio]benzene

HRID 1791874Notes

Reaction equation

HRID 1791874 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[SH:35]>CCO>[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[S:35][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 11430Potassium CarbonateHCID 22033501HCID 22033501, compound

Product 1

HCID 22033547Amino-2-[2-(4-cyanophenyl)ethylthio]benzeneYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Toluenesulfonic acid, 2-(4-cyanophenyl)ethyl ester (1.9 g; 6.3 mmol; from Example 18(i) above) and K2CO3 (2.0 g) were added to a solution of 2-aminothiophenol (0.875 g; 7.0 mmol) in EtOH (20 mL). The mixture was heated to reflux for 48 hours, cooled, filtered and concentrated in vacuo to an oil which was dissolved in EtOAc (50 mL) and washed with water (25 mL). The organic portion was dried (MgSO4) and concentrated. The residue was purified by flash chromatography (SiO2; Et2O:hexane (1:1)) to obtain 1.32 g (78%) of the sub-title product as a viscous oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 48 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to an oil which
  6. dissolutionwas dissolved in EtOAc (50 mL)
  7. washwashed with water (25 mL)
  8. dry with materialThe organic portion was dried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography (SiO2; Et2O:hexane (1:1))

Sources & evidence

ORD record
ord-aca5d9a5cf0247d095e0826dbde90a3e
Source dataset
uspto-grants-2006_07
Patent number
US07074820B2

Reaction notes

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