Sodium Hydroxide → 4-Chloro-2-{[2-chloro-4-(ethylsulfonyl)phenyl]thio}aniline

HRID 910835Notes

Reaction equation

HRID 910835 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]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 673916204-Chloro-2-{[2-chloro-4-(ethylsulfonyl)phenyl]thio}-1-nitrobenzene

Product 1

HCID 673913764-Chloro-2-{[2-chloro-4-(ethylsulfonyl)phenyl]thio}aniline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe filtrate evaporated under reduced pressure
  3. customto give a brown oil which
  4. extractionextracted with ethyl acetate
  5. customThe organics were dried
  6. customevaporated under reduced pressure
  7. customthe residue purified by chromatography on silica eluting with isohexane/ethylacetate 2:1, yield 0.70 g

Sources & evidence

ORD record
ord-6a7813e3f86c462a816d715d542eae55
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

Loading…