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

HRID 843299Notes

Reaction equation

HRID 843299 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-].[Na+].[Na+]>[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 10340Sodium CarbonateHCID 122074-IodotolueneHCID 15240193HCID 15240193, compound

Product 1

HCID 151237584-(5H-Dibenzo[a,d]cyclohepten-5-ylidenemethyl)-N,N-bis(4-methylphenyl)benzenamineYield 149.9%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

To 30 ml of o-dichlorobenzene, were added 7.90 g (26.7 mmol) of the 5-(4-aminobenzylidene)-5H-dibenzo[a,d]cycloheptene previously obtained, 22.0 g (101 mmol) of p-iodotoluene, 11.0 g (79.6 mmol) of anhydrous sodium carbonate and 2.2 g of copper powder. The mixture was refluxed with stirring for 7 hours in an oil bath kept at around 190° C. After the reaction was completed, the reaction was subjected to suction filtration and the filtrate was successively washed with an aqueous 35% sodium thiosulfate solution and saturated brine. The organic layer was dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. To the resulting residue was added about 60 ml of acetone, and the precipitated crystals were collected by filtration. The crystals obtained were further recrystallized using an ethyl acetate/n-hexane mixed solvent to obtain 9.52 g of 5-[4-(di-p-tolylamino)benzylidene)-5H-dibenzo[a,d]cyclo heptene. Yield: 75.0%; m.p.: 168.0 to 169.0° C.

Workup

  1. custompreviously obtained
  2. temperatureThe mixture was refluxed
  3. customkept at around 190° C
  4. filtrationthe reaction was subjected to suction filtration
  5. washthe filtrate was successively washed with an aqueous 35% sodium thiosulfate solution and saturated brine
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. additionTo the resulting residue was added about 60 ml of acetone
  9. filtrationthe precipitated crystals were collected by filtration
  10. customThe crystals obtained
  11. customwere further recrystallized

Sources & evidence

ORD record
ord-7e6bd88b3c7d430fbea8e2e6e15442e9
Source dataset
uspto-grants-2002_04
Patent number
US06376695B1

Reaction notes

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