9,10-Anthracenedione, 2-amino-3-chloro- → Anthrimide

HRID 1414218

Reaction equation

[NH2:1][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](Cl)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[N+](C1C=CC=CC=1)([O-])=O.C(=O)([O-])[O-].[Na+].[Na+].N[C:39]1[C:52]2[C:51](=[O:53])[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:44](=[O:54])[C:43]=2[CH:42]=[C:41](Cl)[CH:40]=1>>[CH:10]1[CH:9]=[C:8]2[C:7]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([NH:1][C:42]4[C:43]5[C:44]([C:45]6[C:50]([C:51](=[O:53])[C:52]=5[CH:39]=[CH:40][CH:41]=4)=[CH:49][CH:48]=[CH:47][CH:46]=6)=[O:54])[C:15]=3[C:14](=[O:16])[C:13]2=[CH:12][CH:11]=1)=[O:17]

Participants

Reactant 5

HCID 67719,10-Anthracenedione, 2-amino-3-chloro-

HCID 7416Nitrobenzene

HCID 10340Sodium Carbonate

HCID 178841-Amino-4-chloro-9,10-anthracenedione

HCID 24386Thionyl Chloride

Product 1

HCID 6700Anthrimide

Procedure

21 g of 6-chloro-2-(4-diphenyl)-anthrapyrimidine (obtained by reacting 1-amino-4-chloroanthraquinone with diphenyl-4-carboxylic acid N-methylamide in the presence of thionyl chloride (in accordance with D.R.P. 566,474)) are condensed, in accordance with Example 1, in 250 parts of nitrobenzene in the presence of 7.5 parts of sodium carbonate and 0.25 part of copper-1 chloride with 13.5 parts of 1-amino-3-chloroanthraquinone. 28 parts are obtained of the anthrimide of the formula ##SPC9##

Workup

customcondensed

Sources & evidence

ORD record: ord-9382bbe1a6aa4dd395b41c896390f9e5
Source dataset: uspto-grants-1977_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04001170

Linked notes

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