1-Chloro-4-nitrobenzene → N,N,N',N'-Tetrakis(4-aminophenyl)-1,4-benzenediamine

HRID 1183249Notes

Reaction equation

[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([NH2:8])[CH:2]=1.Cl[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1>>[NH2:7][C:6]1[CH:5]=[CH:4][C:3]([N:8]([C:3]2[CH:2]=[CH:1][C:6]([NH2:7])=[CH:5][CH:4]=2)[C:10]2[CH:15]=[CH:14][C:13]([N:16]([C:10]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=3)[C:10]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=3)=[CH:12][CH:11]=2)=[CH:2][CH:1]=1

Participants

Reactant 2

HCID 74741-Chloro-4-nitrobenzene

HCID 7814P-Phenylenediamine

Product 1

HCID 76776N,N,N',N'-Tetrakis(4-aminophenyl)-1,4-benzenediamine

Procedure

Such a diimonium compound can be synthesized, for example, as follows. That is, an Ullmann reaction product of p-phenylenediamine and 1-chloro-4-nitrobenzene, is reduced to obtain N,N,N′,N′-tetrakis(p-aminophenyl)-p-phenylenediamine which is then dissolved in N,N-dimethylformamide, and an alkyl bromide is added thereto, followed by a reaction, for example, at 130° C. for 10 hours.

Sources & evidence

ORD record: ord-cd93a9a0bba24425a0c99081ba9d8440
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664309B2

Reaction notes

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