Reacción #2049

Ecuación de reacción

5-[N-(4-tolyl)amino]acenaphthene

5-[N-(4-tolyl)amino]acenaphthene

iodo benzene

potassium carbonate

nitrobenzene

→

5-[N-(4-tolyl)-N-phenylamino]acenaphthene

Rendimiento 83.8%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISSOLUTIONto dissolve the reaction product
2. 2
   Filtraciónthe mixture was filtrated
3. 3
   Concentraciónconcentrated
4. 4
   OtroThe concentrated material thus obtained
5. 5
   Otrowas purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4)

Procedimiento

4.66 g (0.018 mol) of the above prepared 5-[N-(4-tolyl)amino]acenaphthene was mixed with 4.99 g (0.022 mol) of iodo benzene, 0.13 g (0.002 mol) of copper powder, 2.76 g (0.02 mol) of anhydrous potassium carbonate and 5 ml of nitrobenzene, and the resultant mixture was stirred at 200° C. for 25 hours. The reaction was determined to be finished when disappearance of 5-[N-(4-tolyl)amino]acenaphthene was identified. 100 ml of toluene was added thereto to dissolve the reaction product, and the mixture was filtrated and concentrated. The concentrated material thus obtained was purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4) to obtain 5.06 g (yield: 83.8%, melting point: 147.0°-148.0° C.) of 5-[N-(4-tolyl)-N-phenylamino]acenaphthene.

Fuente