4,4'-Dimethoxydiphenylamine → 1,1-bis(p-2,2,2-trifluoroethoxyphenyl)-2-[N,N-bis-(4-methoxyphenyl)amino]ethylene

HRID 326968

Reaktionsgleichung

Reaktionsgleichung von HRID 326968
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[OH2:18].[C:19]1(C)[CH:24]=[CH:23][C:22](S(O)(=O)=O)=[CH:21][CH:20]=1.[F:30][C:31]([F:44])([F:43])[CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH:41]=O)=[CH:36][CH:35]=1>C1(C)C=CC=CC=1>[F:30][C:31]([F:44])([F:43])[CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]([C:19]2[CH:20]=[CH:21][C:22]([O:18][CH2:32][C:31]([F:44])([F:43])[F:30])=[CH:23][CH:24]=2)=[CH:41][N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:36][CH:35]=1

Komponenten

5

Edukt 3

HCID 75714,4'-DimethoxydiphenylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 131718270p-2,2,2-Trifluoroethoxyphenylacetaldehyde

Produkt 1

HCID 200977531,1-bis(p-2,2,2-trifluoroethoxyphenyl)-2-[N,N-bis-(4-methoxyphenyl)amino]ethylene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Using a 30-ml flask similar to that used in Production Example 1, 0.65 g (2.84 mmole) of 4.4'-dimethoxydiphenylamine and 5 mg of p-toluenesulfonic acid monohydrate were added to 10 ml anhydrous toluene solution containing 1.11 g (2.84 mmole) of 1,1-bis(p-2,2,2-trifluoroethoxyphenylacetaldehyde under a nitrogen atmosphere, and refluxed for 3 hours while dehydrating using molecular sieves 4A. After cooling to room temperature, the solution was filtered and the solvent was distilled off. The residue was purified using an alumina column (toluene). The resulting white solid was recrystallized from hexane to yield white crystals of 1,1-bis(p-2,2,2-trifluoroethoxyphenyl)-2-[N,N-bis-(4-methoxyphenyl)amino]ethylene [Compound (4)] in an amount of 1.46 g (yield 85%).

Aufarbeitung

  1. temperaturerefluxed for 3 hours
  2. filtrationthe solution was filtered
  3. distillationthe solvent was distilled off
  4. customThe residue was purified
  5. customThe resulting white solid was recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-03bf23159666400c9536128491479c88
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05272030

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