2-Chloro-5-nitrobenzenesulfonic acid → 4,4'-Diaminodiphenyl Ether

HRID 1071895Notes

Reaction equation

HRID 1071895 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-])=O)=[C:6](S(O)(=O)=O)[CH:7]=1.O[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=1S(O)(=O)=O.ClC1C=CC([N+]([O-])=O)=C(S(O)(=O)=O)C=1.ClC1C=CC([N+]([O-])=O)=CC=1S(O)(=O)=O.[OH-].[Na+]>[C].[Pd]>[CH:6]1[C:5]([NH2:12])=[CH:4][CH:3]=[C:2]([O:1][C:16]2[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=2)[CH:7]=1

Participants

7

Reactant 5

HCID 73102-Chloro-5-nitrobenzenesulfonic acidHCID 14798Sodium HydroxideHCID 692252-Hydroxy-5-nitrobenzenesulphonic acidHCID 134631585-Chloro-2-nitrobenzene-1-sulfonic acidHCID 22389735HCID 22389735, compound

Product 1

HCID 75794,4'-Diaminodiphenyl Ether

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

A 5-hydroxy-2-nitrobenzenesulfonic acid derivative (e.g. sodium 5-hydroxy-2-nitrobenzenesulfonate) or a 2-hydroxy-5-nitrobenzenesulfonic acid derivative (e.g. sodium 2-hydroxy-5-nitrobenzenesulfonate) is reacted with a 5-chloro-2-nitrobenzenesulfonic acid derivative or a 2-chloro-5-nitrobenzenesulfonic acid derivative in the presence of an alkali (e.g. sodium hydroxide), followed by hydrogenation using palladium-carbon, to give the corresponding 4,4′-diaminodiphenyl ether derivative. This is diazotized using sodium nitrite under acidic conditions in the presence of hydrochloric acid, followed by reaction with sodium azide, to give the desired product.

Sources & evidence

ORD record
ord-e08b178ce0d141aba33801356614f0b7
Source dataset
uspto-grants-2005_06
Patent number
US06908719B1

Reaction notes

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