4-Trimethylsilyloxyaniline → 2-[1-(2,4,6-Trimethylphenylimino)ethyl]-6-[1-(4-trimethylsiloxyphenylimino)ethyl]pyridine

HRID 49753Notes

Reaction equation

HRID 49753 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].[CH3:22][Si:23]([CH3:33])([CH3:32])[O:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=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:29][C:28]2[CH:27]=[CH:26][C:25]([O:24][Si:23]([CH3:33])([CH3:32])[CH3:22])=[CH:31][CH:30]=2)[CH3:20])[N:14]=1)[CH3:12]

Participants

4

Reactant 2

HCID 5972734-TrimethylsilyloxyanilineHCID 221344681-{6-[(1E)-N-(2,4,6-Trimethylphenyl)ethanimidoyl]pyridin-2-yl}ethan-1-one

Product 1

HCID 213000452-[1-(2,4,6-Trimethylphenylimino)ethyl]-6-[1-(4-trimethylsiloxyphenylimino)ethyl]pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Monoimine (1, 1.4 g, 5 mmol) and 4-trimethylsiloxyaniline (8, 906 mg, 5 mmol) were dissolved in 50 ml of toluene. To this solution 4 Å molecular sieves were added. After standing at room temperature for 4 days with addition of more molecular sieves the reaction mixture was filtered and the solvent was removed in vacuo. The product was washed with a small amount of methanol. Yield 1.4 g (63%) of mixed diimine (9). 1H NMR (CDCl3) δ 8.42 (dd, 1H), 8.33 (dd, 1H), 7.86 (t, 1H), 6.88 (s, 2H), 6.86 (d, 2H), 6.74 (d, 2H), 2.42 (s, 3H), 2.28 (s, 3H), 2.21 (s, 3H), 2.00 (s, 6H), 0.27 (s, 9H).

Workup

  1. additionTo this solution 4 Å molecular sieves were added
  2. additionAfter standing at room temperature for 4 days with addition of more molecular sieves the reaction mixture
  3. filtrationwas filtered
  4. customthe solvent was removed in vacuo
  5. washThe product was washed with a small amount of methanol

Sources & evidence

ORD record
ord-cbed8da99e36459e8881f383c689b52f
Source dataset
uspto-grants-2004_03
Patent number
US06710006B2

Reaction notes

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