2,6-Diethylaniline → HCID 57587138, compound

HRID 889551Notes

Reaction equation

HRID 889551 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].[CH2:22]([C:24]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][CH3:32])[C:25]=1[NH2:26])[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:26][C:25]2[C:27]([CH2:31][CH3:32])=[CH:28][CH:29]=[CH:30][C:24]=2[CH2:22][CH3:23])[CH3:20])[N:18]=1)[CH3:12]

Participants

4

Reactant 2

HCID 113692,6-Diethylaniline2×HCID 594646241-{6-[1-(2-Chloro-4,6-dimethylphenylimino)ethyl]pyridin-2-yl}ethanone

Product 1

HCID 57587138HCID 57587138, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.00 g of 1-{6-[1-(2-chloro-4,6-dimethylphenylimino)-ethyl]pyridin-2-yl}ethanone (3.3 mol), 0.99 g of 2,6-diethylaniline (6.6 mmol) and 1.0 g of Sicapent were heated under reflux under argon in 50 ml of tetrahydrofuran for 2 h. A further portion of Sicapent (0.5 g) was added and the mixture was heated under reflux under argon for a further 1.5 h. A further portion of Sicapent (0.5 g) and 0.50 g of 2,6-diethylaniline (3.3 mmol) were added and the mixture was heated under reflux under argon for a further 15 h and then cooled to room temperature. The reaction mixture was filtered and the residue on the filter was washed with 10 ml of tetrahydrofuran. The filtrate was topped up to 125 ml with tetrahydrofuran, 4 g of Sicapent were added and the mixture was heated again under reflux under argon for 2.5 h and then cooled to room temperature. It was filtered and the residue on the filter was washed with 10 ml of tetrahydrofuran. The solvent was then distilled off completely and the residue was stirred with 10 ml of methanol. The precipitate formed was filtered off and washed twice with methanol. After drying in vacuo, 0.36 g (0.8 mmol) of 2-[1-(2-chloro-4,6-dimethylphenylimino)ethyl]-6-[1-(2,6-diethylphenylimino)ethyl]pyridine was obtained in a yield of 25%.

Workup

  1. additionA further portion of Sicapent (0.5 g) was added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux under argon for a further 1.5 h
  4. temperaturethe mixture was heated
  5. temperatureunder reflux under argon for a further 15 h
  6. filtrationThe reaction mixture was filtered
  7. washthe residue on the filter was washed with 10 ml of tetrahydrofuran
  8. additionwere added
  9. temperaturethe mixture was heated again
  10. temperatureunder reflux under argon for 2.5 h
  11. temperaturecooled to room temperature
  12. filtrationIt was filtered
  13. washthe residue on the filter was washed with 10 ml of tetrahydrofuran
  14. distillationThe solvent was then distilled off completely
  15. customThe precipitate formed
  16. filtrationwas filtered off
  17. washwashed twice with methanol
  18. customAfter drying in vacuo

Sources & evidence

ORD record
ord-daac0c3659054512b990adc419e6c1f4
Source dataset
uspto-grants-2012_08
Patent number
US08252875B2

Reaction notes

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