Nitrobenzene → 1-(4'-Methyl-3'-nitrophenylamino)-4-phenylmercaptoanthraquinone

HRID 1704311

Reaktionsgleichung

Reaktionsgleichung von HRID 1704311
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[N+](C1C=CC=CC=1)([O-])=O.Br[C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[C:43]([N+:48]([O-:50])=[O:49])[CH:42]=1>>[CH3:47][C:44]1[CH:45]=[CH:46][C:41]([NH:1][C:2]2[C:15]3[C:14](=[O:16])[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:7](=[O:17])[C:6]=3[C:5]([S:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:4][CH:3]=2)=[CH:42][C:43]=1[N+:48]([O-:50])=[O:49]

Komponenten

5

Edukt 4

HCID 7416NitrobenzeneHCID 10340Sodium CarbonateHCID 835231-Amino-4-(phenylthio)anthraquinoneHCID 1235464-Bromo-2-nitrotoluene

Produkt 1

HCID 227591911-(4'-Methyl-3'-nitrophenylamino)-4-phenylmercaptoanthraquinoneAusbeute 90 %

Versuchsvorschrift

A mixture of 23.2 parts of 1-amino-4-phenylmercaptoanthraquinone, 9 parts of sodium carbonate and 150 parts of nitrobenzene is heated to the boil, whilst stirring, and dehydrated in the course of one hour, whilst a stream of nitrogen is passed through. 30 parts of 4-bromo-2-nitrotoluene and 1 part of copper-I chloride are then added to the mixture, which has been cooled to 150°. After stirring for 15 hours at 150° and, at the same time, passing a moderate stream of nitrogen through the mixture, the reaction mixture is allowed to cool. The reaction product is precipitated by gradually adding 200 parts of methanol and is filtered off, washed with methanol and hot water and finally boiled thoroughly with 5% strength hydrochloric acid. This gives 29.5 parts (90% of theory) of 1-(4'-methyl-3'-nitrophenylamino)-4-phenylmercaptoanthraquinone with a melting point of 199°-201°. The colorant dyes polyester violet in bulk.

Aufarbeitung

  1. temperatureis heated to the boil
  2. customdehydrated in the course of one hour, whilst a stream of nitrogen
  3. temperaturehas been cooled to 150°
  4. stirringAfter stirring for 15 hours at 150° and, at the same time
  5. temperatureto cool
  6. customThe reaction product is precipitated
  7. additionby gradually adding 200 parts of methanol
  8. filtrationis filtered off
  9. washwashed with methanol and hot water

Quellen und Nachweise

ORD-Eintrag
ord-c180d3b994584db3aaf42ce79ae6e2cb
Quelldatensatz
uspto-grants-1978_11
Patentnummer
US04126626

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