Benzamide, N-(4-chloro-9,10-dihydro-9,10-dioxo-1-anthracenyl)- → HCID 20384810, compound

HRID 2082860Notes

Reaction equation

HRID 2082860 reaction equation
Cl[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]([NH:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[Cl:27][C:28]1[CH:34]=[C:33]([N+:35]([O-:37])=[O:36])[CH:32]=[CH:31][C:29]=1[NH2:30].C(=O)([O-])[O-].[Na+].[Na+].ClC1C=CC=CC=1Cl>[Cu]I.C1(C)C=CC=CC=1.N1C=CC=CC=1>[Cl:27][C:28]1[CH:34]=[C:33]([N+:35]([O-:37])=[O:36])[CH:32]=[CH:31][C:29]=1[NH:30][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]([NH:18][C:19](=[O:26])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6679Benzamide, N-(4-chloro-9,10-dihydro-9,10-dioxo-1-anthracenyl)-HCID 72391,2-DichlorobenzeneHCID 84922-Chloro-4-nitroanilineHCID 10340Sodium Carbonate

Product 1

HCID 20384810HCID 20384810, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

36.15 parts of 1-chloro-4-benzoylaminoanthraquinone, 21.6 parts of 2-chloro-4-nitroaniline and 10 parts of sodium carbonate are stirred in 400 parts of o-dichlorobenzene. A solution of 0.4 part of copper-(I) iodide in 5 parts of pyridine, and 25 parts of toluene, are added and the mixture is heated to the boil -- 160° to 165°. The water liberated is distilled off azeotropically and the toluene is recirculated. After a reaction time of 45 minutes, the reaction product begins to precipitate. The mixture is stirred for 7 hours at 160°-165° and is then allowed to cool. The precipitate is filtered off, washed with o-dichlorobenzene, acetone and hot water, and extracted by boiling with dilute hydrochloric acid. 34.4 parts of 1-(2'-chloro-4'-nitroanilino)-4-benzoylaminoanthraquinone are obtained in the form of a dark powder. The colorant bulk-dyes PES in claret-colored shades of good fastness properties.

Workup

  1. temperaturethe mixture is heated to the boil
  2. custom160° to 165°
  3. distillationThe water liberated is distilled off azeotropically
  4. customAfter a reaction time of 45 minutes
  5. customto precipitate
  6. temperatureto cool
  7. filtrationThe precipitate is filtered off
  8. washwashed with o-dichlorobenzene, acetone and hot water
  9. extractionextracted

Sources & evidence

ORD record
ord-faa28471124e4ba3969a5b516f5b8e3b
Source dataset
uspto-grants-1978_04
Patent number
US04082778

Reaction notes

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