1-{6-[(1E)-N-(2,4,6-Trimethylphenyl)ethanimidoyl]pyridin-2-yl}ethan-1-one → HCID 22134473, compound

HRID 1986025Notes

Reaction equation

HRID 1986025 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].[CH2:22]([O:42][C:43]1[C:49]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[CH:48][C:46]([NH2:47])=[CH:45][C:44]=1[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>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:47][C:46]2[CH:45]=[C:44]([C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[C:43]([O:42][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[C:49]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[CH:48]=2)[CH3:20])[N:14]=1)[CH3:12]

Participants

4

Reactant 2

HCID 221344681-{6-[(1E)-N-(2,4,6-Trimethylphenyl)ethanimidoyl]pyridin-2-yl}ethan-1-oneHCID 22134479HCID 22134479, compound

Product 1

HCID 22134473HCID 22134473, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-[1-(2,4,6-trimethylphenylimino)ethyl]-6-acetyl pyridine (3 g, 10.7 mmol), prepared according to the method disclosed in WO02/28805, and 4-eicosanoxy-3,5-diphenylaniline (5.8 g, 10.7 mmol) were dissolved in 200 ml of toluene. To this solution, 4 Å molecular sieves were added. After standing for 1 day the mixture was filtered. The solvent was removed in vacuo. The residue was crystallised from cold ethanol. The product, D, was isolated as a yellow treacle (6.5 g, 8.1 mmol, 76%) after drying at 60° C. in vacuo.

Workup

  1. additionTo this solution, 4 Å molecular sieves were added
  2. filtrationthe mixture was filtered
  3. customThe solvent was removed in vacuo
  4. customThe residue was crystallised from cold ethanol
  5. customThe product, D, was isolated as a yellow treacle (6.5 g, 8.1 mmol, 76%)
  6. customafter drying at 60° C. in vacuo

Sources & evidence

ORD record
ord-86750a9de4184f9da22ea239eb2767e6
Source dataset
uspto-grants-2009_06
Patent number
US07547783B2

Reaction notes

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