Benzenesulfonyl chloride, 4-chloro-3-nitro- → 3-amino-4-chlorobenzenethiol

HRID 556753Notes

Reaction equation

HRID 556753 reaction equation
[Sn](Cl)Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=O)=O)=[CH:7][C:6]=1[N+:15]([O-])=O.C([O-])(O)=O.[Na+].C(Cl)(Cl)Cl.CCCCCC>Cl.O>[NH2:15][C:6]1[CH:7]=[C:8]([SH:11])[CH:9]=[CH:10][C:5]=1[Cl:4]

Participants

7

Reactant 4

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 21585165Chloroform hexane

Product 1

HCID 6406993-amino-4-chlorobenzenethiolYield 60%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a cooled solution (0° C.) of tin(II) chloride (11.260 g, 59.40 mmol) in 10 ml concentrated hydrochloric acid was slowly added 4-chloro-3-nitro-benzenesulfonyl chloride (1.690 g, 6.60 mmol) portionwise. The resulting suspension was kept cool and stirred for 15 minutes before the mixture was heated to reflux for 1 hour. After cooling to room temperature the mixture was diluted with water (100 ml) and carefully neutralised using NaHCO3. The aqueous phase was extracted with chloroform (4×50 ml) and the organic phase separated and dried over Na2SO4. Removal of solvent under vacuum afforded a bright yellow solid. Column chromatography on silica gel using 1:1 chloroform/hexane as the mobile phase afforded 3-amino-4-chlorobenzene thiol as a white solid (0.632 g, 60%).

Workup

  1. temperatureThe resulting suspension was kept cool
  2. temperaturewas heated
  3. temperatureto reflux for 1 hour
  4. extractionThe aqueous phase was extracted with chloroform (4×50 ml)
  5. customthe organic phase separated
  6. dry with materialdried over Na2SO4
  7. customRemoval of solvent under vacuum
  8. customafforded a bright yellow solid

Sources & evidence

ORD record
ord-1acacae20c384dcfbea8643626e8be22
Source dataset
uspto-grants-2011_11
Patent number
US08058311B2

Reaction notes

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