4-(Dimethylamino)Benzaldehyde → HCID 14670646, compound

HRID 2396407Notes

Reaction equation

HRID 2396407 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:12][N:13]([CH3:31])[C:14]1[CH:19]=[CH:18][C:17]([CH:20]([C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=2)[CH3:21])=[CH:16][CH:15]=1>C(O)C>[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([C:7]([C:17]2[CH:16]=[CH:15][C:14]([N:13]([CH3:31])[CH3:12])=[CH:19][CH:18]=2)=[CH:21][CH:20]([CH:21]=[C:20]([C:17]2[CH:16]=[CH:15][C:14]([N:13]([CH3:12])[CH3:31])=[CH:19][CH:18]=2)[C:22]2[CH:23]=[CH:24][C:25]([N:28]([CH3:29])[CH3:30])=[CH:26][CH:27]=2)[C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH3:29])[CH3:30])=[CH:24][CH:23]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 2404834,4'-ethane-1,1-diylbis(n,n-dimethylaniline)

Product 1

HCID 14670646HCID 14670646, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Proceeding in a manner similar to that described in Example 1 above, a mixture 1.5 g of 4-dimethylaminobenzaldehyde, 5.4 g of 1,1-bis(4-dimethylaminophenyl)ethane, 100.0 ml of ethyl alcohol and 2.0 ml of glacial aacetic acid was maintained at reflux approximately forty-two hours. After cooling to ambient temperature, the reaction mixture was poured into one liter of ice water, and the resulting solid was collected by filtration and recrystallized from isopropyl alcohol to obtain 2.5 g of bis{[1,1-bis(4-dimethylaminophenyl)ethenyl]}(4-dimethylaminophenyl)methane, a white solid which melted at 215°-220° C. Significant infrared maxima appeared at 1620 cm-1 (v.s.) and 1355 cm-1. The nuclear magnetic resonance spectrum was in accord with the assigned structure. An acetone solution of the product spotted onto clay, phenolic resin and organic acid coated papers slowly developed blue-colored images. Exposure of a paper coated with the product to bromine vapor developed a dark blue image. An acetone solution of the product, chloranil and a phenolic resin was coated onto a glass plate and dried. The transmission spectrum of the coating had a significant adsorption at 715 nonometers.

Workup

  1. temperaturewas maintained
  2. temperatureat reflux approximately forty-two hours
  3. filtrationthe resulting solid was collected by filtration
  4. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-41a254a034e44072891f028fc909e9b9
Source dataset
uspto-grants-1996_02
Patent number
US05491262

Reaction notes

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