p-Toluenesulfonic acid → 2-[1-(2,4,6-Trimethylphenylimino)ethyl]-6-[1-(4-tert-butylphenylimino)ethyl]pyridine

HRID 349595Notes

Reaction equation

HRID 349595 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]=[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=O)[CH3:20])[N:14]=1)[CH3:12].[C:22]([C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]=[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=[N:30][C:29]2[CH:31]=[CH:32][C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:27][CH:28]=2)[CH3:20])[N:14]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 698614-Tert-ButylanilineHCID 221344681-{6-[(1E)-N-(2,4,6-Trimethylphenyl)ethanimidoyl]pyridin-2-yl}ethan-1-one

Product 1

HCID 213000472-[1-(2,4,6-Trimethylphenylimino)ethyl]-6-[1-(4-tert-butylphenylimino)ethyl]pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Monoimine (1, 2.8 g, 10 mmol) and 4-tert-butylaniline (1.49 g, 10 mmol) (ex. Aldrich) were dissolved in 100 ml of toluene. To this solution, 4 Å molecular sieves and a small amount of p-toluenesulphonic acid (0.1 mmol) (ex. Aldrich) were added. After standing for 5 days with addition of more 4 Å molecular sieves, the mixture was refluxed for 2 h. After filtration the solvent was removed in vacuo. The residue was washed with methanol and recrystallised from ethanol. Yield 2.4 g (58%) of mixed diimine (2). 1H-NMR (CDCl3) δ 8.42 (d, 1H, Py-Hm), 8.34 (d, 1H, Py-Hm), 7.86 (t, 1H, Py-Hp), 7.38 (d, 2H, ArH), 6.89 (s, 2H, ArH), 6.78 (d, 2H, ArH), 2.42 (s, 3H, Me), 2.29 (s, 3H, Me), 2.22 (s, 3H, Me), 2.00 (s, 6H, Me), 1.34 (s, 9H, But).

Workup

  1. additionAfter standing for 5 days with addition of more 4 Å molecular sieves
  2. temperaturethe mixture was refluxed for 2 h
  3. filtrationAfter filtration the solvent
  4. customwas removed in vacuo
  5. washThe residue was washed with methanol
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-6141bdcc4ebf4fe781b9f838f4be649f
Source dataset
uspto-grants-2007_02
Patent number
US07179871B2

Reaction notes

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