Benzylamine → 2,5-Diaminobenzenesulfonamide

HRID 731215Notes

Reaction equation

HRID 731215 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 16 and 18) can be treated with a benzylic amine, such as benzylamine, 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-f17a5d9463ca416e97eb89c77b507873
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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