Methanesulfonic Acid → 2,5-Diamino-benzenesulfonamide methanesulfonate

HRID 424179Notes

Reaction equation

HRID 424179 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].[CH3:15][S:16]([OH:19])(=[O:18])=[O:17]>[Pd].C(O)C.O>[CH3:15][S:16]([OH:19])(=[O:18])=[O:17].[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 2

HCID 6395Methanesulfonic AcidHCID 153583862-Amino-5-nitrobenzenesulfonamide

Product 1

HCID 251646412,5-Diamino-benzenesulfonamide methanesulfonateYield 93.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

2-Amino-5-nitrobenzenesulfonamide (prepared as described in Example 1b, 100.00 g, 0.460 mol) and 5% palladium on carbon (wet, 5.00 g) were suspended in ethanol (2 L) and water (100 mL). Methanesulfonic acid (33 mL, 0.51 mol) was added, and the resulting mixture was heated to 55° C. and stirred under atmospheric hydrogen for 8 h. The mixture was filtered and the filtrate was concentrated in vacuo to a volume of about 450 mL. To the concentrate was added acetonitrile (1 L) and resulting mixture was stirred at 25° C. overnight. The suspension was filtered to afford the desired product, 2,5-diamino-benzenesulfonamide methanesulfonate (122.36 g, 0.432 mol, 93.8%) as a purple solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo to a volume of about 450 mL
  3. additionTo the concentrate was added acetonitrile (1 L)
  4. customresulting mixture
  5. stirringwas stirred at 25° C. overnight
  6. filtrationThe suspension was filtered

Sources & evidence

ORD record
ord-d544b615911d49c19377179fe1137464
Source dataset
uspto-grants-2012_01
Patent number
US08101800B2

Reaction notes

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