2,6-Diacetylpyridine → 2,6-Bis[1-(2-chloro-4,6-dimethylphenylimino)ethyl]pyridine

HRID 409614

Reaction equation

HRID 409614 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH3:11])[N:5]=1)(=O)[CH3:2].[Cl:13][C:14]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:15]=1[NH2:16]>C1COCC1>[Cl:13][C:14]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:15]=1[N:16]=[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[N:16][C:15]2[C:17]([CH3:22])=[CH:18][C:19]([CH3:21])=[CH:20][C:14]=2[Cl:13])[CH3:11])[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 707902,6-DiacetylpyridineHCID 1130332-Chloro-4,6-dimethylaniline2×

Product 1

HCID 580977402,6-Bis[1-(2-chloro-4,6-dimethylphenylimino)ethyl]pyridineYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 2,6-diacetylpyridine (35 g, 0.21 mol) in THF (1.21) was added 2-chloro-4,6-dimethylaniline (76.7 g, 2.3 eq) and Sicapent (45 g). The reaction mixture was refluxed overnight. Then additional 2-chloro-4,6-dimethylaniline (25 g, 0.7 eq) and Sicapent (25 g) were added and once again refluxed overnight. The suspension was cooled to 22° C., filtered and washed with two times THF (75 ml). The mother liquor was concentrated (90%) and methanol was added to precipitate the product, which was washed two times with methanol (50 ml) and dried under high vacuum. 68.8 g of a yellow powder was isolated (y=73.1%)

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. filtrationfiltered
  3. washwashed with two times THF (75 ml)
  4. concentrationThe mother liquor was concentrated (90%) and methanol
  5. additionwas added
  6. customto precipitate the product, which
  7. washwas washed two times with methanol (50 ml)
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-afeb893ab894431d89fb4142e79dd804
Source dataset
uspto-grants-2014_06
Patent number
US08759460B2

Linked notes

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