[CH3:1][NH:2][CH:3]=[N:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[CH3:12].[S:13](Cl)Cl.[CH3:16][NH:17][CH:18]=[N:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=1[CH3:27]>CCCCCC.C(N(CC)CC)C.C(Cl)Cl>[CH3:12][C:6]1[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=1[N:4]=[CH:3][N:2]([S:13][N:17]([CH3:16])[CH:18]=[N:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=1[CH3:27])[CH3:1]To a solution of 9.13 g. (0.05 mole) of N-methyl-N'-(2-methyl-4-chlorophenyl)formamidine in 200 ml. of methylene chloride is added 5.05 g. (0.05 mole) of triethylamine. The reaction mixture is cooled to -10° C. and a solution of 5.15 g. (0.05 mole) sulfur dichloride in 5 ml. methylene dichloride is added dropwise keeping the temperature below 0° c. After addition the reaction mixture is allowed to warm to 15° C. About two-thirds of the methylene chloride is removed and 200 ml. of hexane added. The remainder of the methylene chloride is removed and an additional 100 ml. of hexane added. This suspension containing the formamidine sulfenyl chloride is added quickly to a solution of 8.1 g. (0.05 mole) N-methyl-N'-2,4-xylylformamidine and 5.05 g. triethylamine in 300 ml. of hexane with cooling and stirring. The reaction mixture is stirred for 1 hour at room temperature, filtered, and the solvent removed to leave a solid. The crude product is taken up in 200 ml. hexane solution and extracted with 6 g. of citric acid in 100 ml. of water. The hexane solution is dried over MgSO4, filtered, the solvent removed, and the residue recrystallized from Skellysolve B to yield 3.5 g. (18.6%) of product, m.p. 96°-98° C.
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