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

HRID 3693Notes

Reaction equation

HRID 3693 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-18a0ff4af7384269a935d5430d7f8ca8
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Reaction notes

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