Aniline → 3,4-Dimethyl-N,N-diphenylaniline

HRID 1393708Notes

Reaction equation

HRID 1393708 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=1[CH3:16])[NH2:12]>ClC1C=CC=CC=1>[CH3:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=1[CH3:16])[N:12]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 72483,4-Dimethylaniline

Product 1

HCID 186995143,4-Dimethyl-N,N-diphenylaniline

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

An improved process for producing triarylamines directly from an aniline is to react an arylchloride with an aniline compound in the presence of a suitable catalyst. For example, 3,4-dimethylaniline can be rapidly reacted with chlorobenzene to form 3,4-dimethyl-N,N-diphenylaniline using palladium acetate ligated with 2,4,6-trioxa-1,3,5,7-tetramethyl-8-phosphaadamantane, which is manufactured as Cytop-216 (Cytec Industries), and sodium t-pentoxide base. This reaction proceeds rapidly, in about 4 to 8 hours to produce the desired triarylamine.

Sources & evidence

ORD record
ord-2cb2748d227f423cbcb11fecc86d2d5d
Source dataset
uspto-grants-2008_03
Patent number
US07345203B1

Reaction notes

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