[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](Cl)=[O:6].[CH3:10][C:11]1[NH:12][C:13](=[O:17])[CH2:14][S:15][CH:16]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(#N)C>[CH3:10][C:11]1[NH:12][C:13](=[O:17])[CH2:14][S:15][C:16]=1[CH:21]1[CH:22]=[CH:23][N:18]([C:5]([O:4][CH2:3][C:2]([Cl:9])([Cl:8])[Cl:1])=[O:6])[CH:19]=[CH:20]12,2,2-Trichloroethylchloroformate (64 ml) was added dropwise to a stirred suspension of 5-methyl-2H-1,4-thiazin-3(4H)-one (50 g) in a mixture of acetonitrile (500 ml)-pyridine (75 ml) under ice-cooling. The mixture was stirred at room temperature for 1 hour and then, poured into cold water (1.5 l) The resulting precipitates were collected by filtration, recrystallized from ethanol to give 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one (120 g, yield 80.7%) as pale yellow prisms.
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