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

HRID 325053Notes

Reaction equation

HRID 325053 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-33ffd13a03974ccc9cd55a3d7d722357
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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