Nitrobenzene → 1-(2-Chloro-4-nitroanilino)-5-methoxyanthracene-9,10-dione

HRID 2082862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2082862
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([O:17][CH3:18])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=1[Cl:30].C(=O)([O-])[O-].[Na+].[Na+].[N+](C1C=CC=CC=1)([O-])=O>[Cu]Cl>[Cl:30][C:22]1[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=[CH:26][C:21]=1[NH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([O:17][CH3:18])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 7416NitrobenzeneHCID 10340Sodium CarbonateHCID 346671-Bromo-2-chloro-4-nitrobenzeneHCID 138979031-Amino-5-methoxyanthracene-9,10-dione

Produkt 1

HCID 203605261-(2-Chloro-4-nitroanilino)-5-methoxyanthracene-9,10-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 62652Cuprous chlorideKatalysator

Versuchsvorschrift

12.65 parts of 1-amino-5-methoxyanthraquinone, 15.3 parts of 1-bromo-2-chloro-4-nitrobenzene, 5 parts of sodium carbonate and 1 part of copper-(I) chloride in 120 parts of nitrobenzene are stirred for 3 hours at 170°. To remove the water formed during the reaction, a stream of nitrogen is passed through the apparatus during the reaction. After cooling the reaction mixture to 25°, the 1-(2'-chloro-4'-nitroanilino)-5-methoxyanthraquinone formed is filtered off, washed with nitrobenzene, ethanol and hot water and extracted by boiling with 5% strength hydrochloric acid. The colorant is obtained in a yield of 19.5 parts, that is to say 95% of theory. It bulk-dyes polyester in an orange-coloured shade having excellent fastness properties.

Aufarbeitung

  1. customTo remove the water
  2. customformed during the reaction
  3. customa stream of nitrogen is passed through the apparatus during the reaction
  4. temperatureAfter cooling the reaction mixture to 25°

Quellen und Nachweise

ORD-Eintrag
ord-2c689383312e40a5a1fd3218eee2f46d
Quelldatensatz
uspto-grants-1978_04
Patentnummer
US04082778

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