Benzylamine → 2,5-Diaminobenzenesulfonamide

HRID 730472Notes

Reaction equation

HRID 730472 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-a5ba2389ef5e41d99458618e8de42767
Source dataset
uspto-grants-2009_09
Patent number
US07582754B2

Reaction notes

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