P-Cymene → HCID 19829028, compound

HRID 1493841Notes

Reaction equation

HRID 1493841 reaction equation
[C:1]([NH:4][C:5]1[CH:26]=[CH:25][C:8]([CH:9]=[C:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH:14]=[CH:13][C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]2=3)=[CH:7][CH:6]=1)(=O)[CH3:2].IC1C=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(C(C)C)=CC=1>[Cu]>[C:31]1([CH3:34])[CH:30]=[CH:29][C:1]([NH:4][C:5]2[CH:26]=[CH:25][C:8]([CH:9]=[C:10]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[CH:14]=[CH:13][C:12]4[CH:21]=[CH:22][CH:23]=[CH:24][C:11]3=4)=[CH:7][CH:6]=2)=[CH:2][CH:32]=1

Participants

6

Reactant 4

HCID 7463P-CymeneHCID 11430Potassium CarbonateHCID 122074-IodotolueneHCID 19829027HCID 19829027, compound

Product 1

HCID 19829028HCID 19829028, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

8.0 g (23.7 m moles) of the thus obtained 5-(4-acetylaminobenzylidene)-5H-dibenzo[a,d]cycloheptene, 7.75 g (35.5 m moles) of p-iodotoluene, 3.70 g (26.8 m moles) of anhydrous potassium carbonate and 1.80 g of copper powder were added to 15 ml of p-cymene and stirred and refluxed for 5 hours. After the end of reaction, the reaction mixture was subjected to filtration by suction, and the filtrate was successively washed with an aqueous 3-5% sodium thiosulfate solution and an aqueous saturated NaCl solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed therefrom under reduced pressure. The residue was dissolved in 40 ml of tetrahydrofuran and admixed with 2.70 (50.0 m moles) of sodium methylate at room temperature. The mixture as such was stirred at room temperature for one hour, and then the reaction mixture was poured into 150 ml of water. The precipitated crystal was recovered therefrom by filtration, and recrystallized from ethanol-methylethylketone solvent mixture, whereby 5.81 g of 5-[4-(p-tolylamino)benzylidene]-5H-dibenzo[a,d]cycloheptene was obtained (yield: 63.6%). The melting point was 174.0°-175.0° C., and elemental analysis as C29H23N was as follows:

Workup

  1. temperaturerefluxed for 5 hours
  2. customAfter the end of reaction
  3. filtrationthe reaction mixture was subjected to filtration by suction
  4. washthe filtrate was successively washed 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. dissolutionThe residue was dissolved in 40 ml of tetrahydrofuran
  8. customadmixed with 2.70 (50.0 m moles) of sodium methylate at room temperature
  9. stirringThe mixture as such was stirred at room temperature for one hour
  10. additionthe reaction mixture was poured into 150 ml of water
  11. customThe precipitated crystal was recovered
  12. filtrationby filtration
  13. customrecrystallized from ethanol-methylethylketone solvent mixture

Sources & evidence

ORD record
ord-95d64b8c35c243bb85954dbe401f59ea
Source dataset
uspto-grants-1991_06
Patent number
US05024912

Reaction notes

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