[NH2:1][C:2]1[NH:6][N:5]=[C:4]([SH:7])[N:3]=1.C(OC(=O)C)(=[O:10])C.ClCl.Cl[C:18]1[C:24]([CH3:25])=[CH:23][CH:22]=[C:21]([Cl:26])[C:19]=1[NH2:20].[ClH:27].[OH2:28]>C(O)(=O)C>[Cl:27][C:18]1[C:24]([CH3:25])=[CH:23][CH:22]=[C:21]([Cl:26])[C:19]=1[NH:20][S:7]([C:4]1[N:3]=[C:2]([NH2:1])[NH:6][N:5]=1)(=[O:10])=[O:28]A mixture of 11.6 g (0.10 mole) of 5-amino-3-mercapto-1,2,4-triazole, 12.75 g (0.0125 moles) of acetic anhydride and 100 ml of acetic acid was prepared and heated at reflux with stirring for 12 hours. Another 50 ml of acetic acid and 10 ml of water were then added and the mixture was cooled to 12° C. Chlorine (21 g, 0.3 mole) was then added to the mixture with stirring over a 15 min. period at 12°-20° C. A yellow solution was obtained. About 100 ml of volatiles were removed by distillation at 50° C. under reduced pressure. The resulting residue was combined with 2,6-dichloro-3-methylaniline (14.1 g, 0.080 mole) and the mixture heated at 115° C. for 4 hours with stirring. Concentrated aqueous hydrochloric acid (50 ml) was then added and the mixture was heated at reflux with stirring for another 5 hours. It was then allowed to cool to ambient temperature and the solids present were collected by filtration. The collected solids were placed in 200 ml of 10 percent aqueous sodium hydroxide. The insoluble material was removed by filtration and the pH of the filtrate was adjusted to 4.5 with hydrochloric acid to reprecipitate the title compound. The solids were recovered by filtration, washed with water, and dried under reduced pressure to obtain 10.1 g (28.9 percent of theory) of the title compound assaying 95 percent by high pressure liquid chromatography.
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