C(N(CC)CC)C.[CH2:8]([S:10][C:11]1[CH:33]=[CH:32][CH:31]=[CH:30][C:12]=1[C:13]([NH:15][NH:16][C:17](=[O:29])[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:20][CH:19]=1)=O)[CH3:9].[Cl-].ClC1N(C)CC[NH+]1C>C(Cl)Cl>[CH2:8]([S:10][C:11]1[CH:33]=[CH:32][CH:31]=[CH:30][C:12]=1[C:13]1[O:29][C:17]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:20][CH:19]=2)=[N:16][N:15]=1)[CH3:9]Triethylamine (735 μL, 5.28 mmol) was added to a stirring solution of 2-(ethylthio)-N′-(4-pentylbenzoyl)benzohydrazide (1-D) (326 mg, 0.88 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (448 mg, 2.64 mmol) in methylene chloride (10 mL). After stirring at room temperature for 18 h, the mixture was diluted with methylene chloride and washed with water, 1N HCl, 10% NaHCO3, brine, dried (MgSO4) and evaporated in vacuo. The oily residue was purified by preparative TLC (silica gel, hexane:ethyl acetate, 4:1) to provide 2-[2-(ethylthio)phenyl]-5-(4-pentylphenyl)-1,3,4-oxadiazole (1-E).
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