Nitrobenzene → Anthrimide

HRID 542991

反応式

HRID 542991 の反応式
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]

参加物

6

反応物 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)-

生成物 1

HCID 6700Anthrimide

試薬・触媒・溶媒 1

HCID 62652Cuprous chloride触媒2 回

反応条件

温度
190 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6e1789c02387441596e9901a79ae04b6
出典データセット
uspto-grants-1987_04
特許番号
US04659831

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