1-Naphthylamine → 4-(6-(4-Methoxybenzylthio)hexyl)phenyl-1-naphthylamine

HRID 1282537Notes

Reaction equation

HRID 1282537 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.COC1C=CC(C[CH:19]([CH2:47][C:48]2C=CC(Br)=CC=2)[CH2:20][CH2:21][CH2:22][CH2:23][S:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]([CH2:39][C:40]2[CH:45]=[CH:44][C:43](Br)=[CH:42][CH:41]=2)CC2C=CC(OC)=CC=2)=CC=1.[C:57]([O:61][Na])(C)(C)C>C1(C)C(C)=CC=CC=1.[Pd].P>[CH3:57][O:61][C:19]1[CH:20]=[CH:21][C:22]([CH2:23][S:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:39][C:40]2[CH:41]=[CH:42][C:43]([NH:1][C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:5]=[CH:4][CH:3]=3)=[CH:44][CH:45]=2)=[CH:48][CH:47]=1

Participants

6

Reactant 3

HCID 86401-NaphthylamineHCID 701787324-Methoxybenzyl-5-(4-bromobenzyl)pentyl sulfideHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 184246874-(6-(4-Methoxybenzylthio)hexyl)phenyl-1-naphthylamine

Reagents, catalysts & solvents 2

HCID 2241076578452-78-5CatalystHCID 7237O-XyleneSolvent

Procedure

In an orthoxylene solvent, 1-aminonaphthalene was reacted with 4-methoxybenzyl-5-(4-bromobenzyl)pentyl sulfide in the presence of Pd/phosphine and t-butoxy sodium to obtain 4-(6-(4-methoxybenzylthio)hexyl)phenyl-1-naphthylamine. Then, 4,4′-dibromobiphenyl was added into the resultant compound to obtain N,N′-bis(4-(6-(4-methoxybenzylthio)hexyl)phenyl)-N,N′-bis(α-naphtyl)-1,1′-biphenyl-4,4′-diamine through the same reaction. N,N′-bis(4-(6-mercaptohexyl)phenyl)-N,N′-bis(α-naphtyl)-1,1′-biphenyl-4,4′-diamine, the intended product having a mercapto group, was removed from the compound in the presence of anisole in a trifluoroacetic acid. Its structure was confirmed by the elementary analysis or NMR analysis.

Sources & evidence

ORD record
ord-96237a53d51e4110b3473452f749fc1d
Source dataset
uspto-grants-2002_09
Patent number
US06456003B1

Reaction notes

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