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

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

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.