[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[S-:9][C:10]#[N:11].[NH4+].S([O-])(O)=O.[Na+].C(Cl)(Cl)Cl>Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:10]([NH2:11])=[S:9])[CH:6]=[CH:7][CH:8]=1A solution of 3-bromoaniline (10.89 ml, TCI) in 20% aqueous hydrochloric acid (18.2 ml) was added with ammonium thiocyanate (8.02 g, WAKO) and sodium hydrogensulfite (701 mg, WAKO), and stirred at 100° C. for 22 hours. The reaction mixture was added with chloroform (20 ml) for extraction, and the organic layer was dried. Then, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1) to obtain the title compound (Intermediate 74, 4.45 g).
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