[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH2:5][C:6]1[N:10]([CH3:11])[C:9]([CH2:12]O)=[N:8][C:7]=1[CH:14]([CH3:16])[CH3:15].CN(C)C=O.[N-:26]=[N+:27]=[N-:28].[Na+]>S(Cl)(Cl)=O.O>[N:26]([CH2:12][C:9]1[N:10]([CH3:11])[C:6]([CH2:5][C:4]2[CH:3]=[C:2]([Cl:1])[CH:19]=[C:18]([Cl:20])[CH:17]=2)=[C:7]([CH:14]([CH3:16])[CH3:15])[N:8]=1)=[N+:27]=[N-:28]In 5 ml of thionyl chloride was dissolved 160 mg (0.51 mmol) of [5-(3,5-dichlorobenzyl)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methanol (59a), and the mixture was stirred at room temperature. After 2 hours, the reaction mixture was concentrated under reduced pressure, and to the residue, 5 ml of dry dimethylformamide and 80 mg (1.23 mmol) of sodium azide were added. The mixture was stirred at room temperature for 3 hours, diluted with water, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated to give 150 mg of 2-azidomethyl-5-(3,5-dichlorobenzyl)-4-isopropyl-1-methyl-1H-imidazole (60) (yield 87%).
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