Imidazole → 1-Phenethylimidazole

Participants

Reaction Steps

β-Bromoethylbenzene (10 g) and 10.6 g of imidazole were reacted at 200° C. for 5 hours, and the reaction mixture was extracted with 200 ml of chloroform. After being washed with a 10% sodium hydrogen carbonate aqueous solution and then with water, the resultant chloroform layer was separated and dried over salt cake. The solvent was then distilled off under reduced pressure and the residue was purified by distillation under reduced pressure to give 5.50 g (yield 45%) of N-phenethylimidazole as an oily material. B.P. 158° to 159° C./5 mmHg. A solution of 0.43 g of the obtained N-phenethylimidazole in 5 ml of ether was then added to a solution of 2.14 g of α-cyclodextrin in 50 ml of water, and the mixture was stirred at room temperature for 3 hours. The mixture was then lyophilized to give a colorless powder which in turn was washed twice with 50 ml of ether and dried under reduced pressure at 50° C. The product was dissolved in deuterium oxide, and it was confirmed from the proton integration ratio of the proton nuclear magnetic resonance spectra that the product was a clathrate compound of α-cyclodextrin and N-phenethylimidazole in a molar ratio of 1 to 1.

Provenance & Evidence