[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:19]=[CH:18][C:8]2[N:9]=[C:10]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])[S:11][C:7]=2[CH:6]=1.O.[Cl-].[NH4+]>C(O)C>[NH2:24][C:22]1[CH:21]=[CH:20][C:3]([O:4][C:5]2[CH:19]=[CH:18][C:8]3[N:9]=[C:10]([NH:12][C:13]([CH:15]4[CH2:17][CH2:16]4)=[O:14])[S:11][C:7]=3[CH:6]=2)=[C:2]([F:1])[CH:23]=1To a suspension of N-[6-(2-fluoro-4-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide (1.15 g, 3.07 mmol) in ethanol (50 mL)/water (10 mL) were added ammonium chloride (1.64 g, 30.7 mmol) and reduced iron (856 g, 15.3 mmol), and the mixture was heated under reflux for 4 hr. The reaction mixture was cooled to room temperature, filtered through celite, and washed with a mixed solution of ethanol/water. The solvent was evaporated under reduced pressure, 1N aqueous sodium hydroxide solution was added to the residue, and the mixture was extracted 3 times with ethyl acetate/tetrahydrofuran. The combined organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate/diisopropyl ether and collected by filtration to give the title compound (644 mg, 61%) as a pale-yellow solid.
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