N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(3,5-dimethylphenyl)amine → N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(3,5-dimethylphenyl)amine titanium bis(dimethylamide)

HRID 15706Notes

Reaction equation

HRID 15706 reaction equation
[CH3:1][C:2]1[CH:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][NH:17][C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=2)[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].[CH3:26][N:27]([Ti:29](N(C)C)(N(C)C)N(C)C)[CH3:28]>C1(C)C=CC=CC=1>[CH3:16][N-:17][CH3:18].[CH3:26][N-:27][CH3:28].[Ti+2:29].[CH3:1][C:2]1[CH:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][NH:17][C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=2)[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 131727120N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(3,5-dimethylphenyl)amineHCID 178486193HCID 178486193, compound

Product 1

HCID 131727121N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(3,5-dimethylphenyl)amine titanium bis(dimethylamide)Yield 222.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(3,5-dimethylphenyl)amine (4.0 mmol) in toluene (18.4 mL) was added dropwise a solution of tetrakis(dimethylamino)titanium (4.0 mmol) in toluene (12.2 mL) at −78° C. The mixture was stirred at room temperature for 1 hr and then at 100° C. for 5 hrs to give a red solution. The solvent was distilled off under reduced pressure to synthesize N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(3,5-dimethylphenyl)amine titanium bis(dimethylamide) (2.08 g, yield 100%) as a red solid.

Workup

  1. customat 100° C. for 5 hrs to give a red solution
  2. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ce76f66d5b4c4e88b53344e52131fcb7
Source dataset
uspto-grants-2010_06
Patent number
US07732643B2

Reaction notes

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