Nitrobenzene → Anthrimide

HRID 542991

Reaction equation

HRID 542991 reaction equation
C(N[C:10]1[C:23]2[C:22](=[O:24])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:25])[C:14]=2[C:13](Br)=[CH:12][CH:11]=1)(=O)C1C=CC=CC=1.[NH2:27][C:28]1[C:41]2[C:40](=[O:42])[C:39]3[C:34](=[C:35](NC(=O)C4C=CC=CC=4)[CH:36]=[CH:37][CH:38]=3)[C:33](=[O:52])[C:32]=2[CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+].[N+](C1C=CC=CC=1)([O-])=O>[Cu]Cl>[CH:12]1[CH:13]=[C:14]2[C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([NH:27][C:28]4[C:41]5[C:40]([C:39]6[C:34]([C:33](=[O:52])[C:32]=5[CH:31]=[CH:30][CH:29]=4)=[CH:35][CH:36]=[CH:37][CH:38]=6)=[O:42])[C:21]=3[C:22](=[O:24])[C:23]2=[CH:10][CH:11]=1)=[O:25]

Participants

6

Reactant 4

HCID 7416NitrobenzeneHCID 10340Sodium CarbonateHCID 66478Benzamide, N-(4-bromo-9,10-dihydro-9,10-dioxo-1-anthracenyl)-HCID 67011Benzamide, N-(5-amino-9,10-dihydro-9,10-dioxo-1-anthracenyl)-

Product 1

HCID 6700Anthrimide

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst2×

Conditions

Temperature
190 °C

Procedure

55 parts of 1-benzamido-4-bromoanthraquinone, 45 parts of 1-amino-5-benzamidoanthraquinone, 10 parts of sodium carbonate and 1.4 parts of copper(I) chloride are suspended in 550 parts of nitrobenzene. With stirring, the mixture is heated to 190° C. and then a further 1.3 parts of copper(I) chloride are added. The reaction mixture is heated to 205° C. and stirred for 3 hours at this temperature while distilling off the water of reaction. The batch is then heated to 215° C. and the pressure rises to about 1 bar. Stirring is continued for another 2 hours under these conditions. The reaction mixture is then slightly cooled and the nitrobenzene is removed by distillation. The reaction product is dried, affording about 85 parts of anthrimide, which can be converted into a brown vat dye by carbazolation.

Workup

  1. temperatureThe reaction mixture is heated to 205° 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 215° C.
  6. stirringStirring
  7. temperatureThe reaction mixture is then slightly cooled
  8. customthe nitrobenzene is removed by distillation
  9. customThe reaction product is dried

Sources & evidence

ORD record
ord-6e1789c02387441596e9901a79ae04b6
Source dataset
uspto-grants-1987_04
Patent number
US04659831

Linked notes

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