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

Participants

Reaction Steps

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.

Provenance & Evidence