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

HRID 1414218
Notes
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Reaction equation

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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 67719,10-Anthracenedione, 2-amino-3-chloro-HCID 7416NitrobenzeneHCID 10340Sodium CarbonateHCID 178841-Amino-4-chloro-9,10-anthracenedioneHCID 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

  1. customcondensed

Sources & evidence

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

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes