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

HRID 326968

Reaction equation

HRID 326968 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-03bf23159666400c9536128491479c88
Source dataset
uspto-grants-1993_12
Patent number
US05272030

Linked notes

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