Pyridine → HCID 13518417, compound
Reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:8])[CH2:5][S:6][CH:7]=1.Cl[C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH3:1][C:2]1[NH:3][C:4](=[O:8])[CH2:5][S:6][C:7]=1[CH:21]1[CH:22]=[CH:23][N:18]([C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11])[CH:19]=[CH:20]1Participants
4
Procedure
To a solution of 5-methyl-2H-1,4-thiazin-3(4H)-one (1.5 g) in dry pyridine (20 ml), 2,2,2-trichloroethyl chloroformate (2.8 g) was added dropwise under ice bath temperature. The reaction mixture was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure and the residue was extracted with chloroform. The extract was washed with 2N hydrochloric acid and water, and dried over anhydrous magnesium sulfate and chloroform was removed under reduced pressure. The residual oil was triturated with ether and recrystallized from ethanol using decolorizing chacoal to give 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one (1.4 g, yield 31.5%) as light yellow scales.