[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1.[ClH:19].[N:20]([O-])=O.[Na+]>O.O.Cl[Sn]Cl>[ClH:19].[F:1][C:2]([F:17])([F:18])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][NH2:20])=[CH:11][CH:12]=14-[3-(Trifluoromethyl)phenoxy]benzenamine (15 g) was added to a stirred solution of 6 M HCl (190 mL). The resulted suspension was cooled to −5° C., and then an aqueous solution of NaNO2 (4.5 g in 15 mL water) was added dropwise over a period of 15 min. The reaction mixture was stirred for another 30 min, followed by the gradual addition of a solution of SnCl2.2H2O (69 g in 100 mL conc HCl). After stirring at −5° C. for 2 h, the stirred mixture was warmed to room temperature overnight, filtered, and the collected solid was washed with 6 M HCl, water, and dried (18 g).
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