Diisopropylaniline → 2-[1-(2-Chloro-4,6-dimethylphenylimino)ethyl]-6-[1-(2,6-diisopropylphenylimino)ethyl]pyridine

HRID 889552Notes

Reaction equation

HRID 889552 reaction equation
[Cl: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[N:18]=[C:17]([C:19](=O)[CH3:20])[CH:16]=[CH:15][CH:14]=1)[CH3:12].[CH:22]([C:25]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]([CH3:34])[CH3:33])[C:26]=1[NH2:27])([CH3:24])[CH3:23]>O1CCCC1>[Cl: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:14]=[CH:15][CH:16]=[C:17]([C:19](=[N:27][C:26]2[C:28]([CH:32]([CH3:33])[CH3:34])=[CH:29][CH:30]=[CH:31][C:25]=2[CH:22]([CH3:24])[CH3:23])[CH3:20])[N:18]=1)[CH3:12]

Participants

4

Reactant 2

HCID 32484DiisopropylanilineHCID 594646241-{6-[1-(2-Chloro-4,6-dimethylphenylimino)ethyl]pyridin-2-yl}ethanone

Product 1

HCID 575871402-[1-(2-Chloro-4,6-dimethylphenylimino)ethyl]-6-[1-(2,6-diisopropylphenylimino)ethyl]pyridineYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

18.80 g of 1-{6-[1-(2-chloro-4,6-dimethylphenylimino)-ethyl]pyridin-2-yl}ethanone (0.0625 mol), 22.16 g of 2,6-diisopropylaniline (0.125 mol) and 20.0 g of Sicapent were heated under reflux under argon in 300 ml of tetrahydrofuran for 17 h. A further portion of Sicapent (10.0 g) was added and the mixture was heated under argon for a further 4 h and then cooled to room temperature. It was filtered and the residue on the filter was washed with 50 ml of tetrahydrofuran. The solvent was distilled off completely from the combined filtrates and the residue was stirred with 50 ml of methanol. The precipitate formed was filtered off, washed twice with methanol, stirred with 100 ml of hot methanol and then filtered. 17.84 g (0.0388 mol) of 2-[1-(2-chloro-4,6-dimethylphenylimino)ethyl]-6-[1-(2,6-diisopropylphenylimino)ethyl]pyridine were obtained in a yield of 62%.

Workup

  1. additionA further portion of Sicapent (10.0 g) was added
  2. temperaturethe mixture was heated under argon for a further 4 h
  3. filtrationIt was filtered
  4. washthe residue on the filter was washed with 50 ml of tetrahydrofuran
  5. distillationThe solvent was distilled off completely from the combined filtrates
  6. customThe precipitate formed
  7. filtrationwas filtered off
  8. washwashed twice with methanol
  9. stirringstirred with 100 ml of hot methanol
  10. filtrationfiltered

Sources & evidence

ORD record
ord-fc3da06ffa91448b88f8b2515a96b25c
Source dataset
uspto-grants-2012_08
Patent number
US08252875B2

Reaction notes

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