[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:11][NH:12][S:13]([C:16]2[CH:21]=CC(C)=CC=2)(=O)=O)CC)=[CH:4][CH:3]=1.[OH-].[Na+]>S(Cl)(Cl)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:11]=[N:12][S:13][C:16]=2[CH3:21])=[CH:6][CH:7]=1N′-[1-(4-Fluorophenyl)propylidene]-4-methylbenzenesulfonohydrazide (12.0 g) was dissolved in thionyl chloride (30 ml), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into a 1N aqueous sodium hydroxide solution. The precipitated solids were collected by filtration, washed with water and dried with airflow to give 4-(4-fluorophenyl)-5-methyl-1,2,3-thiadiazole (6.19 g, 65%) as a yellow solid.
Loading…