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1-Chloroanthraquinone → Anthrimide

HRID 542992
Notes
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Reaction equation

HRID 542992 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[CH:5]=[CH:4][CH:3]=1.[NH2:18][C:19]1[C:32]2[C:31](=[O:33])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24](=[O:34])[C:23]=2[CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].[N+](C1C=CC=CC=1)([O-])=O>[Cu]Cl>[CH:10]1[CH:9]=[C:8]2[C:7]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([NH:18][C:19]4[C:32]5[C:31]([C:30]6[C:25]([C:24](=[O:34])[C:23]=5[CH:22]=[CH:21][CH:20]=4)=[CH:26][CH:27]=[CH:28][CH:29]=6)=[O:33])[C:15]=3[C:14](=[O:16])[C:13]2=[CH:12][CH:11]=1)=[O:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 67091-ChloroanthraquinoneHCID 67101-AminoanthraquinoneHCID 7416NitrobenzeneHCID 10340Sodium Carbonate

Product 1

HCID 6700Anthrimide

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst2×

Conditions

Temperature
190 °C

Procedure

66 parts of 1-chloroanthraquinone, 60.5 parts of 1-aminoanthraquinone, 26.4 parts of sodium carbonate and 0.75 part of copper(I) chloride are suspended in 550 parts of nitrobenzene. With stirring, the mixture is heated to 190° C. and then a further 0.75 part of copper(I) chloride is added. The reaction mixture is heated to 206° C. and stirred for 3 hours at this temperature while distilling off the water of reaction. The batch is then heated to 214° C. and the pressure rises to about 1 bar. Stirring is continued for another 2 hours under these conditions. The reaction mixture is then cooled slightly and the nitrobenzene is removed by distillation. After drying there are obtained about 115 parts of anthrimide, which is suitable for further processing to give vat dyes.

Workup

  1. temperatureThe reaction mixture is heated to 206° C.
  2. stirringstirred for 3 hours at this temperature
  3. distillationwhile distilling off
  4. customthe water of reaction
  5. temperatureThe batch is then heated to 214° C.
  6. stirringStirring
  7. temperatureThe reaction mixture is then cooled slightly
  8. customthe nitrobenzene is removed by distillation
  9. customAfter drying there

Sources & evidence

ORD record
ord-9c2fec673e5f4601a85c0970a6f0fdfc
Source dataset
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04659831

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes