1-Chloro-4-nitrobenzene → 4,4'-Diaminodiphenyl Ether

HRID 1071899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071899
[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)=CC=1.[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

6

Edukt 4

HCID 74741-Chloro-4-nitrobenzeneHCID 14798Sodium HydroxideHCID 692252-Hydroxy-5-nitrobenzenesulfonic 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 4-chloronitrobenzene 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-f2a7d5f82f14418588c8952d1bd63b0e
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908719B1

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