4-Amino-6-chloro-1,3-benzenedisulfonamide → 4-Aminobenzene-1,3-disulfonamide

HRID 496145Notes

Reaction equation

HRID 496145 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[C:5]([S:9](=[O:12])(=[O:11])[NH2:10])=[CH:4][C:3]=1[S:13]([NH2:16])(=[O:15])=[O:14]>CCO.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:9](=[O:11])(=[O:12])[NH2:10])=[CH:4][C:3]=1[S:13]([NH2:16])(=[O:15])=[O:14]

Participants

4

Reactant 1

HCID 671364-Amino-6-chloro-1,3-benzenedisulfonamide

Product 1

HCID 130719484-Aminobenzene-1,3-disulfonamideYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred suspension of 2-amino-4-chloro-5-sulfamoylbenzenesulfonamide (11.4 g; 40 mmol) and 10% Pd/C (750 mg) in EtOH (300 ml) was hydrogenated at 1 bar until hydrogen consumption ceased (24 h). The reaction mixture was evaporated to dryness, resuspended in THF and filtered through celite. The filtrate was evaporated to dryness and the isolated solid washed with boiling EtOAc (2×150 ml) to give 9.58 g (95%) product.

Workup

  1. customwas hydrogenated at 1 bar until hydrogen consumption
  2. custom(24 h)
  3. customThe reaction mixture was evaporated to dryness
  4. filtrationfiltered through celite
  5. customThe filtrate was evaporated to dryness
  6. washthe isolated solid washed with boiling EtOAc (2×150 ml)

Sources & evidence

ORD record
ord-19ebd848cceb401c9ec0d18a8c9e1831
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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