N-benzyl-4-nitrobenzenesulfonamide → Benzylsulfamide

HRID 497310Notes

Reaction equation

HRID 497310 reaction equation
[CH2:1]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Pd]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 745343N-benzyl-4-nitrobenzenesulfonamide

Product 1

HCID 66909BenzylsulfamideYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-benzyl-4-nitrobenzenesulfonamid (60 g, 1 eq) was dissolved in anhydrous ethanol (2 l) and Pd/C (10 g, 1 eq) was added under inert atmosphere. The mixture was stirred under a hydrogen atmosphere for 8 h. Then the solution was filtered over Celite, concentrated in vacuo to ˜40 ml and then crystallized. The product was washed twice with ethanol (20 ml) at 4° C., filtered and dried in vacuo to give 4-amino-N-benzylbenzenesulfonamide. Yield 75%.

Workup

  1. filtrationThen the solution was filtered over Celite
  2. concentrationconcentrated in vacuo to ˜40 ml
  3. customcrystallized
  4. washThe product was washed twice with ethanol (20 ml) at 4° C.
  5. filtrationfiltered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-fa8f763304db437ca1bad9a8a25a4082
Source dataset
uspto-grants-2005_09
Patent number
US06949567B2

Reaction notes

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