Potassium Carbonate → 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidenemethyl)-N,N-bis(4-methylphenyl)benzenamine

HRID 1493840Notes

Reaction equation

HRID 1493840 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH:6]=[C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH:11]=[CH:10][C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]2=3)=[CH:4][CH:3]=1.I[C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].ClC1C=CC=CC=1Cl>[C:28]1([CH3:31])[CH:29]=[CH:30][C:25]([N:1]([C:2]2[CH:23]=[CH:22][C:5]([CH3:6])=[CH:4][CH:3]=2)[C:2]2[CH:23]=[CH:22][C:5]([CH:6]=[C:7]3[C:8]4[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=4[CH:10]=[CH:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]3=4)=[CH:4][CH:3]=2)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122074-IodotolueneHCID 15240193HCID 15240193, compound

Product 1

HCID 151237584-(5H-Dibenzo[a,d]cyclohepten-5-ylidenemethyl)-N,N-bis(4-methylphenyl)benzenamineYield 75%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

7.90 g (26.7 m moles) of the previously obtained 5-(4-amino-benzylidene)-5H-dibenzo[a,d]cycloheptene, 22.0 g (101 m mole) of p-iodotoluene, 11.0 g (79.6 m moles) of anhydrous potassium carbonate and 2.2 g of copper powder were added to 30 ml of o-dichlorobenzene, and the resulting mixture was stirred and refluxed over an oil bath kept at about 190° C. for 7 hours. After the end of reaction, the reaction mixture was subjected to filtration by suction, and the filtrate was washed successively with an aqueous 3-5% sodium thiosulfate solution and an aqueous saturated NaCl solution. The organic layer was dried over anhydrous sodium sulfate and then the solvent was removed therefrom under reduced pressure. The residue was admixed with about 60 ml of acetone, and the precipitated crystal was recovered therefrom by filtration, and recrystallized from ethyl acetate-n-hexane solvent mixture, whereby 9.52 g of 5-[4(di-p-tolylamino)benzylidene]-5H-dibenzo[a,d]cycloheptene was obtained (yield: 75.0%). The melting point was 168.0°-169.0° C. Elemental analysis as C36H29N was as follows:

Workup

  1. temperaturerefluxed over an oil bath
  2. customAfter the end of reaction
  3. filtrationthe reaction mixture was subjected to filtration by suction
  4. washthe filtrate was washed successively with an aqueous 3-5% sodium thiosulfate solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed
  7. customthe precipitated crystal was recovered
  8. filtrationby filtration
  9. customrecrystallized from ethyl acetate-n-hexane solvent mixture

Sources & evidence

ORD record
ord-7ffbb3872f8c4653b19ca9854d4575b4
Source dataset
uspto-grants-1991_06
Patent number
US05024912

Reaction notes

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