HCID 14716236, compound → HCID 54529923, compound

HRID 375510Notes

Reaction equation

HRID 375510 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:14]2[CH:19]=[CH:18][C:17]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:16][CH:15]=2)=[CH:11][CH:12]=O)=[CH:6][CH:5]=1)[CH3:2].[CH3:27][C:28]([CH3:31])([O-])[CH3:29].[K+]>CN(C=O)C>[CH2:1]([N:3]([CH2:25][CH3:26])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:14]2[CH:19]=[CH:18][C:17]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:16][CH:15]=2)=[CH:11][CH:12]=[CH:27][C:28]2[CH:31]=[CH:31][C:28]([CH:27]=[CH:12][CH:11]=[C:10]([C:14]3[CH:15]=[CH:16][C:17]([N:20]([CH2:21][CH3:22])[CH2:23][CH3:24])=[CH:18][CH:19]=3)[C:7]3[CH:8]=[CH:9][C:4]([N:3]([CH2:25][CH3:26])[CH2:1][CH3:2])=[CH:5][CH:6]=3)=[CH:29][CH:29]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14716236HCID 14716236, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54529923HCID 54529923, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 100 ml of DMF were dissolved 2.5 g of 3,3-bis(p-diethylaminophenyl)acrolein and 1.5 g of p-xylene-α,α'-diylbis(diethyl phosphonate), and then 0.9 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 with stirring. 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 1.74 g (yield 63.0%) of red crystals having a melting point of 201.5° C. to 204.5° C.

Workup

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

Sources & evidence

ORD record
ord-e609ec385bab418e83da9f4bf32e9a79
Source dataset
uspto-grants-1996_01
Patent number
US05486441

Reaction notes

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