HCID 19990421, compound → HCID 19990419, compound

HRID 346162Notes

Reaction equation

HRID 346162 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:11][C:10]=1[N+:19]([O-:21])=O)([C:3](OCC)=[O:4])=[O:2]>C(O)C.[Pt]>[OH:21][N:19]1[C:10]2[C:9](=[CH:14][CH:13]=[C:12]([S:15](=[O:17])(=[O:16])[NH2:18])[CH:11]=2)[NH:8][C:1](=[O:2])[C:3]1=[O:4]

Participants

4

Reactant 1

HCID 19990421HCID 19990421, compound

Product 1

HCID 19990419HCID 19990419, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 4-ethoxalylamino-3-nitrobenzenesulfonamide (1.59 g, 5 mmol) in 300 ml of 96% ethanol was hydrogenated at atmospheric pressure and room temperature for 30 min. in the presence of 50 mg of 5% platinum on carbon. The catalyst was filtered off and the filtrate was evaporated to dryness. The residue was washed with ethanol and dissolved in 25 ml of saturated aqueous ammonium hydroxide. An undissolved orange residue was removed by filtration, and most of the ammonia was removed from the filtrate under reduced pressure. After treatment with decolourising carbon the filtrate was acidified with conc. hydrochloric acid to give 0.76 g (59%) of the title compound as an off-white precipitate. M.p.>250° C. decomp. (DSC); NMR (DMSO-d6): 7.07-7.93 (m, 3H, ArH), 7.33 (broad s, 2H, NH2), ca. 11.9 (very broad s, 1H, NH or OH), 12.3 (broad s, 1H, OH or NH); IR (KBr): 3300-2100, 1690 cm -1 ; MS (m/e): 257 (10%, M+).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. washThe residue was washed with ethanol
  4. dissolutiondissolved in 25 ml of saturated aqueous ammonium hydroxide
  5. customAn undissolved orange residue was removed by filtration
  6. custommost of the ammonia was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-fc4c391544b241279ac70d82b45f186d
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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