2-Iodotoluene → 1,3-Benzenediamine, N,N,N',N'-tetrakis(3-methylphenyl)-

HRID 1084299Notes

Reaction equation

HRID 1084299 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)[CH:9]=2)[CH:2]=1.I[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30].C(=O)([O-])[O-].[K+].[K+]>[N+](C1C=CC=CC=1)([O-])=O.[Cu]>[C:1]1([CH3:22])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]([C:3]2[CH:2]=[C:1]([CH3:22])[CH:6]=[CH:5][CH:4]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N:14]([C:29]3[CH:24]=[C:25]([CH3:30])[CH:26]=[CH:27][CH:28]=3)[C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)[CH:9]=2)[CH:2]=1

Participants

6

Reactant 3

HCID 51282-IodotolueneHCID 11430Potassium CarbonateHCID 20063167HCID 20063167, compound

Product 1

HCID 40817791,3-Benzenediamine, N,N,N',N'-tetrakis(3-methylphenyl)-

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7416NitrobenzeneSolvent

Procedure

More specifically, resorcinol of formula (A) is reacted with m-toluidine of formula (B) in the presence of iodine in a nitrogen current to obtain N,N'-di(3-tolyl)-1,3-phenylenediamine of formula (C). Then, N,N'-di(3-tolyl)-1,3-phenylenediamine is reacted with iodotoluene of formula (D) in the presence of potassium carbonate and powdery copper under reflux in nitrobenzene to obtain N,N,N',N'-tetra(3-tolyl)-1,3-phenylenediamine of formula (E).

Sources & evidence

ORD record
ord-faed9cc48bc844fab861dd9e7e3c11a3
Source dataset
uspto-grants-1991_04
Patent number
US05004662

Reaction notes

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