Toluene → 4-Methyl-N-(4-methylphenyl)-N-{4-[2-(4-methylphenyl)ethenyl]phenyl}aniline

HRID 1178867Notes

Reaction equation

HRID 1178867 reaction equation
O([C:3]([CH3:6])([CH3:5])[CH3:4])[Na].[NH2:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[CH2:13])=[CH:10][CH:9]=1.I[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1.[C:24]1([CH3:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCOC(C)=O.[CH3:37][CH2:38][CH2:39]CCC>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:4][C:3]1[CH:6]=[CH:39][C:38]([N:7]([C:27]2[CH:28]=[CH:29][C:24]([CH3:30])=[CH:25][CH:26]=2)[C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[CH:13][C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[CH:10][CH:9]=2)=[CH:37][CH:5]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 122074-IodotolueneHCID 737004-AminostyreneHCID 21226206Ethyl acetate hexaneHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 542295924-Methyl-N-(4-methylphenyl)-N-{4-[2-(4-methylphenyl)ethenyl]phenyl}anilineYield 87%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Following the general procedure, Pd2dba3 (18.3 mg, 2 mol %), NaO-t-Bu (336 mg, 3.5 mmol), P(isoBuNCH2CH2)3N (13.6 mg, 4 mol %), 4-aminostyrene (119 mg, 1 mmol), 4-Iodotoluene (698 mg, 3.2 mmol), and 10 mL of dry toluene at 110° C. for 16 h. produced (5) N,N-bis(4-methylphenyl)-4-[2-(4-methylphenyl) ethenyl]benzenamine (338 mg, 87%) as the sole product after chromatography with 1% EtOAc/hexane mixture. (See Entry 9 of Table 2).

Workup

  1. customat 110° C.
  2. customfor 16 h.

Sources & evidence

ORD record
ord-c5eb7f2892f946b183bf40b2d77f607c
Source dataset
uspto-grants-2007_10
Patent number
US07276627B2

Reaction notes

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