[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[CH:16][N+:17]([O-:19])=[O:18])=[CH:6][N:5]=1.[H][H].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]Cl)=[CH:25][CH:24]=1>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[C:16]([S:29][C:26]2[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=2)[N+:17]([O-:19])=[O:18])=[CH:6][N:5]=10.2 g of sodium hydride 60% in oil was added to a solution of 1.3 g of 1-(2-chloro-5-pyridylmethyl)-2-nitromethyleneimidazolidine in 15 ml of dry dimethylformamide, and the mixture was stirred at room temperature until the generation of hydrogen gas ceased. 0.9 g of 4-chlorobenzenesulfenylchloride was then drop into the solution at 0° C. with stirring. After stirring for 1 hour at room temperature, the reaction mixture was poured into ice water. The precipitated crystal was filtered and recrystalized from ethyl acetate to give 1-(2-chloro-5-pyridylmethyl)-2-{(4-chlorophenylthio)nitromethylene}imidazolidine. The yield was 1.3 g.
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