C1(C)C=CC=CC=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:17])=CC=1.[C:30]([NH:33][NH:34][C:35](=O)[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([I:42])[CH:37]=1)(=O)[CH3:31].O>C(OCC)(=O)C>[I:42][C:38]1[CH:37]=[C:36]([C:35]2[S:17][C:30]([CH3:31])=[N:33][N:34]=2)[CH:41]=[CH:40][CH:39]=1Toluene (4.1 mL) and Lawesson's reagent (366 mg, 0.904 mmol) were added to N′-acetyl-3-iodobenzohydrazide (250 mg, 0.822 mmol) obtained in Step 1, and the mixture was stirred at 120° C. for 1 hour. After cooling, water and ethyl acetate were added to the mixture to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give 2-(3-iodophenyl)-5-methyl-1,3,4-thiadiazole (150 mg, 60%).
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