Potassium Hydroxide → 2-Chloro-6-(2-chloro-6-nitrophenylthio)aniline

Reaction equation

[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[SH:9].[OH-].[K+].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[C:14]=1Cl>CCO>[Cl:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([S:9][C:14]2[C:15]([N+:19]([O-:21])=[O:20])=[CH:16][CH:17]=[CH:18][C:13]=2[Cl:12])[C:2]=1[NH2:1]

Participants

Procedure

The 2-amino-3-chlorobenzenthiol (550 mg, 3.95 mmol) was dissolved in EtOH (10 mL) followed by KOH (220 mg, 3.95 mmol). To this mixture was added a solution of 1,2-dichloro-3-nitrobenzene (760 mg, 3.95 mmol) in EtOH (10 mL). The resulting reaction mixture was refluxed for 8 h to 12 h. The reaction was allowed to cool to room temperature and the residue was extracted with EtOAc and 1 mol dm−3 H3PO4. The organic layer was dried over MgSO4, filtered and evaporated to give a crude material. This crude material was purified by flash silica gel chromatography.