Diphenylamine → HCID 20525217, compound

HRID 885898Notes

Reaction equation

HRID 885898 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:17][CH:16]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CC(C)([O-])C.[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH2:21]([C:18]1[CH:19]=[CH:20][C:15]([N:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:16][CH:17]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

7

Reactant 4

HCID 11487DiphenylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 151205061-Bromo-4-dodecylbenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 20525217HCID 20525217, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

One equivalent weight of diphenylamine, 1 equivalent weight of 1-bromo-4-dodecylbenzene, 0.1 equivalent weight of palladium(II) acetate, 0.4 equivalent weight of tri(t-butyl)phosphine and 4.8 equivalent weight of potassium t-butoxide were heated in a toluene solution at 90° C. for 2 hours to obtain 4-dodecyl-N,N-diphenylaniline. To the above resultant, 2 equivalent weight of N-bromosuccinimide was added and stirred for 30 minutes at room temperature in N,N-dimethylformamide to obtain 4-dodecyl-N,N-bis(4-bromophenyl)aniline. To the obtained compound, 3 equivalent weight of thiophene boric acid, 0.06 equivalent weight of tetrakis(triphenylphosphine)palladium and 2 equivalent weight of potassium carbonate were added, and heated and refluxed for 3 days in a mixture solvent of THF and water to obtain 4-dodecyl-N,N-bis(4-thiophene-2-yl)phenyl)aniline. To the obtained compound, 5 equivalent weight of phosphorus oxychloride and 5 equivalent weight of N,N-dimethylformamide were added and heated at 105° C. for 5 hours under nitrogen atmosphere for diformylizing the thiophene ring. An acetic acid solution composed of the above obtained diformilized compound, 4 equivalent weight of cyanoacetic acid and 5 equivalent weight of ammonium acetate was heated and refluxed for 1 hour. Thus Dye 1 could be obtained.

Sources & evidence

ORD record
ord-01b7056e3dfb424fa478b45e0e26b9c5
Source dataset
uspto-grants-2012_08
Patent number
US08242355B2

Reaction notes

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