[CH3:1][C:2]1[C:14]([O:15][CH3:16])=[C:13]([CH3:17])[C:5]([CH2:6][S:7][C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)=[C:4]([NH:18][CH2:19][CH2:20][O:21][CH3:22])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:31])C=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.CO>[CH3:1][C:2]1[C:14]([O:15][CH3:16])=[C:13]([CH3:17])[C:5]([CH2:6][S:7]([C:8]2[NH:12][CH:11]=[CH:10][N:9]=2)=[O:31])=[C:4]([NH:18][CH2:19][CH2:20][O:21][CH3:22])[CH:3]=12.00 g (6.2 mmol) of 2-[4,6-dimethyl-5-methoxy-2-(2-methoxyethylamino)benzylthio]imidazole was dissolved in a mixture of 20 ml of chloroform and 2 ml of methanol. To the resulting solution was added 1.27 g of 85 % m-chloroperbenzoic acid under chilling with NaCl-ice for a period of 20 min. After the reaction was completed, chloroform and 5 % aqueous sodium carbonate were added. The organic portion was collected and washed twice with 20 ml of 0.05 N aqueous sodium hydroxide. The resulting mixture was then subject to extraction with 30 ml of 1 N aqueous sodium hydroxide. The aqueous portion was collected and washed with chloroform. To the washed solution was added 45 ml of 1 N aqueous ammonium chloride. The deposited oily product was extracted with dichloromethane. The dichloromethane portion was collected and dried over anhydrous sodium sulfate. Dichloromethane was distilled off and then the residue was crystallized from ether/hexane to give 0.78 g of the desired compound as a pale brown crystalline powder. (Yield: 37 %)
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