[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=2)[CH:5]=[N:4][C:3]=1[CH:20]=[N:21][OH:22].Cl.BrN1C(=O)CCC1=O.[CH2:32]([O:35][CH3:36])[C:33]#[CH:34]>CN(C)C=O.C(N(CC)CC)C>[CH3:36][O:35][CH2:32][C:33]1[O:22][N:21]=[C:20]([C:3]2[N:4]=[CH:5][N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:8]=3)[C:2]=2[CH3:1])[CH:34]=1
660 mg of 5-methyl-1-(3-phenoxyphenyl)-imidazole-4-carbaldehydoxime, hydrochloride is dissolved in 4 ml of dimethylformamide. At 0° C., 0.28 ml of triethylamine is added and a solution of 360 mg of N-bromosuccinimide in 2 ml of dimethylformamide is instilled within one hour. Then, 1.7 ml of methyl propargyl ether and 0.28 ml of triethylamine are added, and the mixture is stirred for 14 hours at room temperature. 360 mg of N-bromosuccinimide in 2 ml of dimethylformamide and 0.28 ml of triethylamine are again added and the mixture is stirred for 18 hours at room temperature. After the concentration by evaporation, it is mixed with water and extracted with ethyl acetate. The extract that has been concentrated by evaporation is mixed with diethyl ether and filtered. The filtrate is purified by column chromatography. 230 mg (32% of theory) of the title compound is obtained as oil.
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