Ethanol → HCID 53868263, compound

HRID 1608261Notes

Reaction equation

HRID 1608261 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:12]=[CH:11][C:6]([CH:7]=[CH:8][CH:9]=O)=[CH:5][CH:4]=1.[CH3:14][N:15]([CH3:33])[C:16]1[CH:21]=[CH:20][C:19]([CH:22]([C:24]2[CH:29]=[CH:28][C:27]([N:30]([CH3:32])[CH3:31])=[CH:26][CH:25]=2)[CH3:23])=[CH:18][CH:17]=1.[CH2:34](O)[CH3:35]>C(O)(=O)C>[CH3:1][N:2]([CH3:13])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([C:35]2[CH:34]=[CH:21][C:16]([N:15]([CH3:33])[CH3:14])=[CH:17][CH:18]=2)=[CH:8][CH:9]([CH:23]=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([N:15]([CH3:14])[CH3:33])=[CH:21][CH:20]=2)[C:24]2[CH:25]=[CH:26][C:27]([N:30]([CH3:31])[CH3:32])=[CH:28][CH:29]=2)[CH:19]=[CH:22][C:24]2[CH:29]=[CH:28][C:27]([N:30]([CH3:32])[CH3:31])=[CH:26][CH:25]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 922244-(Dimethylamino)-cinnamaldehydeHCID 2404834,4'-ethane-1,1-diylbis(n,n-dimethylaniline)2×

Product 1

HCID 53868263HCID 53868263, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 5.7g of 4-dimethylaminocinnamaldehyde, 16.2 g of 1,1-bis(4-dimethylaminophenyl)ethane, 300.0 ml of ethyl alcohol and 6.0 ml of glacial acetic acid was refluxed approximately eighteen hours. After cooling slightly an additional 3.0 g of 1,1-bis(4-dimethylaminophenyl)ethane was added and reflux maintained for an additional four hours. The resulting reaction mixture was cooled to approximately 5° C. and the solid which formed was collected by filtration. The solid was recrystallised from isopropyl alcohol, filtered and dried to obtain 16.3 g of bis{[2,2-bis(4-dimethylaminophenyl)]ethenyl}[2-(4-dimethylaminophenyl)ethenyl]methane (Formula II: R, R1, R3, R4, R9 and R10 =CH3 ; R2, R5 and R11 =H) a yellow solid which melted at 78°-82° C. Significant infrared maxims appeared at 1610 cm-1 (v.s.) and 830 cm-1 (v.s.). An acetone solution of the product spotted onto clay, phenolic resin and organic acid coated papers slowly developed a blue-colored image. Exposure of the spotted papers to bromine vapor increased the speed of color development.

Workup

  1. temperaturewas refluxed approximately eighteen hours
  2. additionwas added
  3. temperaturereflux
  4. temperaturemaintained for an additional four hours
  5. customThe resulting reaction mixture
  6. customthe solid which formed
  7. filtrationwas collected by filtration
  8. customThe solid was recrystallised from isopropyl alcohol
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-c5ae84720e0b43beb72043b3b66607ac
Source dataset
uspto-grants-1989_09
Patent number
US04870050

Reaction notes

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