HRID542991

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7416

Nitrobenzene

C6H5NO2

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：O=C(Nc1ccc(Br)c2c1C(=O)c1ccccc1C2=O)c1ccccc1

HCID66478

Benzamide, N-(4-bromo-9,10-dihydro-9,10-dioxo-1-anthracenyl)-

C21H12BrNO3

结构：Nc1cccc2c1C(=O)c1cccc(NC(=O)c3ccccc3)c1C2=O

HCID67011

Benzamide, N-(5-amino-9,10-dihydro-9,10-dioxo-1-anthracenyl)-

C21H14N2O3

PRODUCTS

生成物

结构：O=C1c2ccccc2C(=O)c2c(Nc3cccc4c3C(=O)c3ccccc3C4=O)cccc21

HCID6700

1,1′-Iminobis[9,10-anthracenedione]

C28H15NO4

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID62652

未命名化合物

2 次

CONDITIONS

反应条件

温度: 190 °C

PROCEDURE

实验过程

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

后处理

temperatureThe reaction mixture is heated to 205° C.
stirringstirred for 3 hours at this temperature
distillationwhile distilling off
customthe water of reaction
temperatureThe batch is then heated to 215° C.
stirringStirring
temperatureThe reaction mixture is then slightly cooled
customthe nitrobenzene is removed by distillation
customThe reaction product is dried

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-6e1789c02387441596e9901a79ae04b6
来源数据集: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04659831
来源说明: uspto-grants-1987_04

反应 SMILES

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]