3,5-Di-tert-butylaniline → HCID 22134478, compound

HRID 1826571Notes

Reaction equation

HRID 1826571 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:27]=[C:28]([CH:30]=[C:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:32]=1)[NH2:29])([CH3:25])([CH3:24])[CH3:23]>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:30]=[C:31]([C:33]([CH3:35])([CH3:34])[CH3:36])[CH:32]=[C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:27]=2)[CH3:20])[N:14]=1)[CH3:12]

Participants

4

Reactant 2

HCID 754193,5-Di-tert-butylanilineHCID 221344681-{6-[(1E)-N-(2,4,6-Trimethylphenyl)ethanimidoyl]pyridin-2-yl}ethan-1-one

Product 1

HCID 22134478HCID 22134478, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-[1-(2,4,6-trimethylphenylimino)ethyl]-6-acetylpyridine (1.3 g, 4.64 mmol), prepared according to the method disclosed in WO02/28805, and 3,5-di-tert-butylaniline (1 g, 4.87 mmol) were dissolved in 100 ml of toluene. To this solution, 4 Å molecular sieves were added. After standing for 2 days the mixture was filtered. The solvent was removed in vacuo. The residue was washed with methanol and crystallised from ethanol. Yield 1.1 g (51%) of 2-[1-(2,4,6-trimethylphenylimino) ethyl]-6-[1-(3,5-di-tert-butylphenylimino)ethyl]pyridine. 1H-NMR (CDCl3) δ 8.43 (d, 1H, Py-Hm), 8.37 (d, 1H, Py-Hm), 7.87 (t, 1H, Py-Hp), 7.16 (t, 1H, ArH), 6.89 (s, 2H, ArH), 6.69 (d, 2H, ArH), 2.42 (s, 3H, Me), 2.29 (s, 3H, Me), 2.22 (s, 3H, Me), 2.01 (s, 6H, Me), 1.33 (s, 18H, But).

Workup

  1. additionTo this solution, 4 Å molecular sieves were added
  2. filtrationthe mixture was filtered
  3. customThe solvent was removed in vacuo
  4. washThe residue was washed with methanol
  5. customcrystallised from ethanol

Sources & evidence

ORD record
ord-419261bff8a844278f6d90496aee6f7d
Source dataset
uspto-grants-2006_05
Patent number
US07053020B2

Reaction notes

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