[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[S-:9][C:10]#[N:11].[Na+].BrBr.[Br-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[Br:1][C:2]1[CH:8]=[C:7]([S:9][C:10]#[N:11])[CH:6]=[CH:5][C:3]=1[NH2:4]To a cold (0°-5° C.), stirred solution of o-bromoaniline (20.6 g., 0.12 mole) and sodium thiocyanate (29.2 g., 0.36 mole) in methanol (300 ml.) is added dropwise a solution of bromine (19.5 g., 0.122 mole) in methanol (75 ml.) saturated with sodium bromide. The solution is stirred for one hour following the addition of the bromine and then poured into water (2 liters) and neutralized with sodium carbonate. The resulting solid is collected, washed with water and dried, m.p. 74°-79° C., yield 96% of theoretical.
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