Benzylamine → 2,5-Diaminobenzenesulfonamide

HRID 2374342Notes

Reaction equation

HRID 2374342 reaction equation
Cl[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].C([NH2:22])C1C=CC=CC=1>>[NH2:22][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[S:11]([NH2:14])(=[O:13])=[O:12]

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 667842-Chloro-5-nitrobenzenesulfonamide

Product 1

HCID 218887652,5-Diaminobenzenesulfonamide

Procedure

The 2-chloro-5-nitro-benzenesulfonamide intermediate (prepared as described in schemes 11 and 12) can be treated with a benzylic amine, such as benzyl amine, to displace the chloro moiety. Hydrogenation under standard conditions can be used to remove the benzylic group and to reduce the nitro group at the same time to afford the desired 2,5-diamino-benzenesulfonamide intermediate.

Workup

  1. customto remove the benzylic group

Sources & evidence

ORD record
ord-6e0fef8870104121b5f76ed5e57fbad0
Source dataset
uspto-grants-2008_12
Patent number
US07462611B2

Reaction notes

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