Réaction #2049

Équation de réaction

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

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

iodo benzene

potassium carbonate

nitrobenzene

→

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

Rendement 83.8%

Solvants

toluene

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source