HCID 18991946, compound → HCID 54129247, compound

HRID 375511Notes

Reaction equation

HRID 375511 reaction equation
[CH2:1]([N:5]([CH2:31][CH2:32][CH2:33][CH3:34])[C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:18][CH:17]=2)=[CH:13][CH:14]=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:35][C:36]([CH3:39])([O-])[CH3:37].[K+]>CN(C=O)C>[CH2:1]([N:5]([CH2:31][CH2:32][CH2:33][CH3:34])[C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:18][CH:17]=2)=[CH:13][CH:14]=[CH:35][C:36]2[CH:39]=[CH:39][C:36]([CH:35]=[CH:14][CH:13]=[C:12]([C:16]3[CH:17]=[CH:18][C:19]([N:22]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:27][CH2:28][CH2:29][CH3:30])=[CH:20][CH:21]=3)[C:9]3[CH:10]=[CH:11][C:6]([N:5]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][CH:8]=3)=[CH:37][CH:37]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 18991946HCID 18991946, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54129247HCID 54129247, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 100 ml of DMF were dissolved 2.21 g of 3,3-bis(p-dibutylaminophenyl)acrolein and 1.0 g of p-xylene-α,α' -diylbis(diethyl phosphonate), and then 0.59 g of potassium tert-butoxide was added to the solution at room temperature. Thereafter, the reaction was carried out for 4 hours at room temperature with stirring and the reaction mixture was poured into 100 ml of ice-water. Then, precipitates thus deposited were collected by filtration, dissolved in benzene, and separated and purified by silica gel column chromatography (eluent: benzene). After distilling off benzene from the effluent, the residue was recrystallized from ethyl acetate to provide 1.42 g (yield 58.8%) of red crystals having a melting point of from 107.0° C. to 111.5° C.

Workup

  1. customThen, precipitates thus
  2. filtrationdeposited were collected by filtration
  3. dissolutiondissolved in benzene
  4. customseparated
  5. custompurified by silica gel column chromatography (eluent: benzene)
  6. distillationAfter distilling off benzene from the effluent
  7. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3c4da4fd8ac94d958cedacb8aae8a1c5
Source dataset
uspto-grants-1996_01
Patent number
US05486441

Reaction notes

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