2,5-Dichlorobenzenesulfonamide → 2-Mercapto-5-Chloro-benzenesulfonamide

HRID 583480Notes

Reaction equation

HRID 583480 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[SH2:13].[Na]>CN(C=O)C>[SH:13][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 2380452,5-DichlorobenzenesulfonamideHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 189353412-Mercapto-5-Chloro-benzenesulfonamideYield 30.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 34.0 g (0.15 mol) of 2,5-dichloro-benzene sulfonamide in 200 mL of DMF was added 16.0 g (0.28 mol) of sodium hydrogensulfide. The mixture was refluxed for 18 hours, then cooled, concentrated, and the solids collected by filtration. The solids were dissolved in hot water, the pH adjusted to 4.0 and the precipitate filtered. This material was dried to yield 10.1 g of the title compound, mp 142-144° C.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. filtrationthe solids collected by filtration
  5. dissolutionThe solids were dissolved in hot water
  6. filtrationthe precipitate filtered
  7. customThis material was dried

Sources & evidence

ORD record
ord-28e1896881ee49b7a24cbcab721e78b9
Source dataset
uspto-grants-1999_07
Patent number
US05929114

Reaction notes

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