Water → 2,5-Diaminobenzenesulfonamide

HRID 731226Notes

Reaction equation

HRID 731226 reaction equation
C([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[S:18]([NH2:21])(=[O:20])=[O:19])C1C=CC=CC=1.O>[Pd].CO>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[S:18]([NH2:21])(=[O:19])=[O:20]

Participants

5

Reactant 2

HCID 962WaterHCID 248583972-Benzylamino-5-nitro-benzenesulfonamide

Product 1

HCID 218887652,5-DiaminobenzenesulfonamideYield 93.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 2-benzylamino-5-nitro-benzenesulfonamide (15 g, 48.81 mmol) and 5% palladium on activated carbon powder (wet, nominally 50% water, 6 g) in methanol (500 mL) was heated to 55° C. The mixture was degassed while stirring and the flask was charged with hydrogen gas via balloon. After stirring for 16 h under 1 atmosphere of hydrogen gas, the reaction was filtered through Celite and concentrated in vacuo to afford the desired product, 2,5-diamino-benzenesulfonamide (8.55 g, 45.67 mmol, 93.6%) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ: 4.56 (2H, bs), 4.98 (2H, bs), 6.58-6.59 (2H, m), 6.87 (1H, d, J=1.6 Hz), 7.00 (2H, s). LC-MS (ESI) calcd for C6H9N3O2S 187.04, found 188.2 [M+H+].

Workup

  1. customThe mixture was degassed
  2. additionthe flask was charged with hydrogen gas via balloon
  3. stirringAfter stirring for 16 h under 1 atmosphere of hydrogen gas
  4. filtrationthe reaction was filtered through Celite
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6435abce535e4262aba94cf48af2c38e
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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