Imidazole → 1-[1-(4-nitrophenyl)ethyl]-1H-imidazole
Reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CS(O[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[CH3:12])(=O)=O>C(#N)C>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([CH:11]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH3:12])=[CH:14][CH:15]=1)([O-:21])=[O:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(a-2) A mixture of 37.5 parts of 1H-imidazole, 61.3 parts of [1-(4-nitrophenyl)ethyl] methanesulfonate and 200 parts of acetonitrile was stirred and refluxed for 2.50 hours. After cooling, the whole was filtered and the filtrate was evaporated. 150 Parts of water were added and the product was extracted three times with 130 parts of dichloromethane. The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 34.4 parts (63.3%) of 1-[1-(4-nitrophenyl)ethyl]-1H-imidazole as a solid residue (int. 113).