Acetic Acid → 4-methyl-1-(3-nitrophenyl)-1H-imidazole

反応式

[N+:1]([C:4]1[CH:5]=[C:6]([N:10]([CH2:13][C:14](=O)[CH3:15])[CH:11]=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C([O-])(=O)C.[NH4+:21].C(O)(=O)C>C1(C)C(C)=CC=CC=1>[CH3:15][C:14]1[N:21]=[CH:11][N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:13]=1

参加物

実験手順

A suspension of N-(3-nitrophenyl)-N-(2-oxo-propyl)-formamide (265 mg), ammonium acetate (919 mg) and acetic acid (0.3 ml) in xylene (5 ml) was refluxed for 2.5 hours and then evaporated under reduced pressure. To the residue were added ethyl acetate and an aqueous solution of sodium hydroxide (1N, 25 ml), and the mixture was stirred for 10 minutes. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated to give 4-methyl-1-(3-nitrophenyl)imidazole (203 mg, 83.9%).