Methacrylic Acid → 4-(N-2-hydroxyethyl-N-ethylamino)-4'-nitro-1,4-diphenyl-1,3-butadiene

HRID 359636

Reaktionsgleichung

Reaktionsgleichung von HRID 359636
[OH:1][CH2:2][CH2:3][N:4](C1C=CC(C=CC=O)=CC=1)[CH2:5][CH3:6].N[C:18]1C=CC=CC=1.[C:24]1([CH3:34])[C:25](S(O)(=O)=O)=[CH:26][CH:27]=[CH:28][CH:29]=1.C(O)(=O)C(C)=C.[N+:41]([C:44]1[CH:49]=[CH:48][C:47]([CH2:50][C:51](O)=O)=[CH:46][CH:45]=1)([O-:43])=[O:42]>C1(C)C=CC=CC=1.O>[OH:1][CH2:2][CH2:3][N:4]([C:50]([C:47]1[CH:46]=[CH:45][C:44]([N+:41]([O-:43])=[O:42])=[CH:49][CH:48]=1)=[CH:51][CH:18]=[CH:34][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:5][CH3:6]

Komponenten

8

Edukt 5

HCID 4093Methacrylic AcidHCID 4661(4-Nitrophenyl)acetic acidHCID 6115AnilineHCID 69252-Methylbenzenesulfonic acidHCID 544515964-(N-2-hydroxyethyl-N-ethylamino)cinnamaldehyde

Produkt 1

HCID 544465724-(N-2-hydroxyethyl-N-ethylamino)-4'-nitro-1,4-diphenyl-1,3-butadiene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 21.9 g (0.1 mole) of 4-(N-2-hydroxyethyl-N-ethylamino)cinnamaldehyde, 9.3 g (1 mole) of aniline, and 0.19 g (1 mole %) of toluenesulfonic acid in toluene is heated at reflux for 17 hours with azeotropic removal of water. After the mixture is cooled to room temperature, 17.2 g (0.2 mole) of methacrylic acid and 18.1 g (0.1 mole) of 4-nitrophenylacetic acid are added to the solution, and the reaction is stirred at room temperature for 3 hours. The mixture then is heated at reflux for 16 hours. After cooling to room temperature, the solid diphenylbutadiene precipitates from solution and is collected by filtration and purified by recrystallization from ethanol.

Aufarbeitung

  1. temperatureThe mixture then is heated
  2. temperatureat reflux for 16 hours
  3. temperatureAfter cooling to room temperature
  4. customthe solid diphenylbutadiene precipitates from solution
  5. filtrationis collected by filtration
  6. custompurified by recrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-662240c8da5d489bacb6f2bba75c3998
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05002361

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