Cl[CH2:2][C:3]([CH2:5]Cl)=O.[C:7]([NH2:13])([NH2:12])=[N:8][C:9]([NH2:11])=[S:10].NC(N)=[S:16].Cl[CH2:19][CH2:20][C:21]#[N:22].[OH-].[Na+]>C(O)(C)C.O.CC(C)=O>[C:21]([CH2:20][CH2:19][S:16][CH2:2][C:3]1[N:11]=[C:9]([NH:8][C:7]([NH2:13])=[NH:12])[S:10][CH:5]=1)#[N:22]Into a 500 mL round bottom flask equipped with an overhead stirrer and under an inert atmosphere was added 25 g of 1,3-dichloroacetone (0.197 mol) and 75 g of acetone. The reaction mixture was cooled to 10° C. and 23.2 g 2-imino-4-thiobiuret (0.197 mol) was added. The reaction mixture was stirred for one hour at 10 C. The reaction mixture was then heated to 40° C. and 15 g of thiourea (0.197 mol) was added, followed by the addition of 100 g of water. The mixture was heated to and held at 52° C. for one hour. Acetone was then removed by vacuum distillation. To the reaction mixture was added 100 g of water, 17 g of 3-chloropropionitrile (0.190 mol) and 40 g of isopropyl alcohol. The reaction mixture was cooled below 10° C. and 25 g of an aqueous solution of sodium hydroxide (80 g water) was added dropwise maintaining the reaction temperature below 10° C. The reaction mixture was for 2 hours, filtered and washed to produce 28 g of N-[4-(cyanoethylthiomethyl)-2-thiazolyl]guanidine product.
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