2-Chloro-4-nitrobenzene-1-thiol → 4-Amino-2-chlorobenzenethiol

HRID 856701Notes

Reaction equation

HRID 856701 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[SH:11]>C(O)(=O)C>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([SH:11])=[C:2]([Cl:1])[CH:7]=1

Participants

3

Reactant 1

HCID 3057302-Chloro-4-nitrobenzene-1-thiol

Product 1

HCID 135193524-Amino-2-chlorobenzenethiolYield 81.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 2-chloro-4-nitrobenzenethiol (4.0 g) was added acetic acid (60 ml), and to this solution was added reduced iron (21 g), and the mixture was stirred at room temperature for 3 hours. The mixture was filtered with Celite, and washed with ethyl acetate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-amino-2-chlorobenzenethiol (2.74 g).

Workup

  1. filtrationThe mixture was filtered with Celite
  2. washwashed with ethyl acetate
  3. customThe solvent was removed under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c6ab9040099e4d329f7525e7abdcf1ae
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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