1,2-Dichlorobenzene → 1-(4-Nitroanilino)-5-(phenylsulfanyl)anthracene-9,10-dione

HRID 1704309Notes

Reaction equation

HRID 1704309 reaction equation
Br[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([S:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:24])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[N+:25]([C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1)([O-:27])=[O:26].C(=O)([O-])[O-].[Na+].[Na+].ClC1C=CC=CC=1Cl>O.N1C=CC=CC=1.C1(C)C=CC=CC=1>[N+:25]([C:28]1[CH:34]=[CH:33][C:31]([NH:32][C:2]2[C:15]3[C:14](=[O:16])[C:13]4[C:8](=[C:9]([S:17][C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[CH:10]=[CH:11][CH:12]=4)[C:7](=[O:24])[C:6]=3[CH:5]=[CH:4][CH:3]=2)=[CH:30][CH:29]=1)([O-:27])=[O:26]

Participants

8

Reactant 4

HCID 72391,2-DichlorobenzeneHCID 74754-NitroanilineHCID 10340Sodium CarbonateHCID 54447464HCID 54447464, compound

Product 1

HCID 227591661-(4-Nitroanilino)-5-(phenylsulfanyl)anthracene-9,10-dione

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

A mixture of 9.87 parts of 1-bromo-5-phenylmercaptoanthraquinone (melting point 191°-193°), 4.32 parts of 4-nitroaniline, 2.5 parts of sodium carbonate, 58 parts of o-dichlorobenzene, 6 parts of toluene and a solution of 0.4 part of copper-I iodide in 1.5 parts of pyridine is heated to the boil (160°-165°) for 24 hours, whilst stirring. The water which is liberated in the course of the reaction is separated off by means of a water separator. After stirring for 3 hours at 20°, the reaction product is filtered off, washed in portions with a little o-dichlorobenzene, then with methanol and also with water and finally heated to the boil with 5% strength hydrochloric acid. After filtering, washing and drying, 9.03 parts, that is to say 80% of theory, of 1-(4'-nitrophenylamino)-5-phenylmercaptoanthraquinone with a melting point of 242°-244° are obtained. The properties of this compound are completely identical to those of the colorant obtained according to Example 1.

Workup

  1. customis separated off by means of a water separator
  2. stirringAfter stirring for 3 hours at 20°
  3. filtrationthe reaction product is filtered off
  4. washwashed in portions with a little o-dichlorobenzene
  5. temperaturewith methanol and also with water and finally heated to the boil with 5% strength hydrochloric acid
  6. filtrationAfter filtering
  7. washwashing
  8. customdrying

Sources & evidence

ORD record
ord-bffdf0fe469346e291c7a2f58cff1c7e
Source dataset
uspto-grants-1978_11
Patent number
US04126626

Reaction notes

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