Diphenylamine → N~9~,N~9~,N~10~,N~10~-Tetraphenylanthracene-9,10-diamine

HRID 1190241Notes

Reaction equation

HRID 1190241 reaction equation
BrC1C=C2C3=C4C(=CC(Br)=CC4=CC=C3C=1)C=C2.C[C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]2[CH:32]=[CH:31][C:30](C)=[CH:29][CH:28]=2)=[CH:22][CH:21]=1.Br[C:35]1[C:36]2[C:41]([C:42](Br)=[C:43]3[C:48]=1[CH:47]=[CH:46][CH:45]=[CH:44]3)=[CH:40][CH:39]=[CH:38][CH:37]=2.[C:50]1([NH:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>>[C:27]1([N:26]([C:23]2[CH:22]=[CH:21][CH:20]=[CH:25][CH:24]=2)[C:35]2[C:36]3[C:41]([C:42]([N:56]([C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)=[C:43]4[C:48]=2[CH:47]=[CH:46][CH:45]=[CH:44]4)=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 4

HCID 11487DiphenylamineHCID 682269,10-DibromoanthraceneHCID 69293Benzenamine, 4-methyl-N-(4-methylphenyl)-HCID 136154792,7-Dibromopyrene

Product 1

HCID 15538838N~9~,N~9~,N~10~,N~10~-Tetraphenylanthracene-9,10-diamine

Procedure

Preparation analogous to Example 20a. Instead of 76.0 g (211 mmol) of dibromopyrene (isomer mixture) and 94.7 g (480 mmol) of bis(4-methylphenyl)amine, 70.9 g (211 mmol) of 9,10-dibromoanthracene and 81.2 g (480 mmol) of diphenylamine are used. Yield: 86.2 g (168 mmol), 79.7% of theory; purity 99% according to 1H-NMR.

Workup

  1. customPreparation analogous to Example 20a

Sources & evidence

ORD record
ord-b6972c9d49234ecfa1e7d5d8ccd60496
Source dataset
uspto-grants-2014_03
Patent number
US08674141B2

Reaction notes

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