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

HRID 1071895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071895
[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

Komponenten

7

Edukt 5

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

Produkt 1

HCID 75794,4'-Diaminodiphenyl Ether

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418390HCID 178418390, VerbindungKatalysator

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-e08b178ce0d141aba33801356614f0b7
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908719B1

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