[F:1][C:2]([S:5][C:6](Cl)=[N:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)([F:4])[F:3].Cl[C:18](=[CH2:21])[C:19]#[N:20].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]2[NH:7][C:6]([S:5][C:2]([F:4])([F:3])[F:1])=[CH:21][C:18]=2[C:19]#[N:20])=[CH:10][CH:11]=1
Under a nitrogen purge, a solution of trifluoromethyl-1-chloro-N-(p-chlorobenzyl)thioformimidate (1.1 g, 0.004 mol) and 2-chloroacrylonitrile (0.4 mL, 0.005 mol) is treated with a solution of triethylamine (1.3 mL, 0.009 mol) in toluene. After an induction period, solids begin to form as the reaction mixture exotherms slightly. When the exotherm subsides, the reaction mixture is heated at reflux temperature for 16 hours, cooled and filtered. The filter cake is washed with ethyl acetate and the filtrate is concentrated in vacuo to obtain a semi-solid. The semi-solid is dissolved in ethyl acetate and the organic solution is washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a solid. The solid is twice recrystallized from 1,2-dichloroethane to give the title product as a beige solid (0.7 g, mp 203°-205° C.) which is identified by 1HNMR spectral analysis.
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