Methanol → 2,5-Diaminobenzenesulfonamide

HRID 424175

Reaction equation

HRID 424175 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[S:11]([NH2:14])(=[O:13])=[O:12].CO.[H][H]>[Pd].O1CCCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[S:11]([NH2:14])(=[O:12])=[O:13]

Participants

6

Reactant 3

HCID 887MethanolHCID 153583862-Amino-5-nitrobenzenesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 218887652,5-DiaminobenzenesulfonamideYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

2-Amino-5-nitro-benzenesulfonamide (5.00 kg, 23.0 mol), methanol (65 L), tetrahydrofuran (65 L), and 10% palladium on carbon (250 g) were charged to an autoclave. The mixture was cycled with nitrogen and hydrogen purges (3×), and the mixture was then stirred under hydrogen (50 psi) at 23° C. overnight. The catalyst was removed by filtration and the filtrate was then concentrated in vacuo to give a brown solid. The solid was further dried in vacuo at 45° C. to afford the desired product, 2,5-diamino-benzenesulfonamide (4.21 kg, 22.4 mol, 98%), as a solid. 1H NMR (400 MHz, DMSO-d6) δ: 4.54 (2H, bs), 4.98 (2H, bs), 6.55-6.60 (2H, m), 6.87 (1H, d, J=2.2 Hz), 6.99 (2H, bs). LC-MS (ESI) calcd for C6H9N3O2S 187.04, found 188.3 [M+H+].

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was then concentrated in vacuo
  3. customto give a brown solid
  4. customThe solid was further dried in vacuo at 45° C.

Sources & evidence

ORD record
ord-2951e247ac8f486f80fbbb031cec501e
Source dataset
uspto-grants-2012_01
Patent number
US08101800B2

Linked notes

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