Sodium Hydroxide → 4-Chloro-2-{[2-chloro-4-(ethylsulfonyl)phenyl]thio}aniline
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([S:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])=[CH:14][C:13]=2[Cl:23])[CH:3]=1.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([S:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])=[CH:14][C:13]=2[Cl:23])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The product from step (ii) (0.80 g) and reduced iron powder (0.80 g) in glacial acetic acid (30 ml) was vigorously stirred at RT for 2 h. The mixture was filtered through celite, and the filtrate evaporated under reduced pressure to give a brown oil which was neutralised with 2M NaOH and extracted with ethyl acetate. The organics were dried, evaporated under reduced pressure and the residue purified by chromatography on silica eluting with isohexane/ethylacetate 2:1, yield 0.70 g.