Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH3:9].ClN1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([O-:39])=[O:38])=[CH:33][CH:32]=1.[Na+].C([O-])(=O)C.[K+]>C(Cl)(Cl)(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][S:37]([C:34]1[CH:35]=[CH:36][C:31]([Cl:30])=[CH:32][CH:33]=1)(=[O:39])=[O:38]A carbon tetrachloride (15 ml) suspension of 4-chloro-3-methylpyridine hydrochloride (402 mg, 2.45 mmol), N-chlorosuccinic acid imide (327 mg, 2.45 mmol) and 2,2′-azobis(2-methylpropionitrile) (30 mg, 0.183 mmol) was heated under reflux for 13 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in butanol (10 ml), followed by the addition of sodium 4-chlorophenylsulfinate (487 mg, 2.45 mmol) and potassium acetate (481 mg, 4.90 mmol). The mixture was stirred at 70° C. for 24 hours. The reaction mixture was cooled to room temperature, followed by concentration under reduced pressure. Ethyl acetate was added to the residue. The mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and brine and then, dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate (=2:1) eluate was concentrated under reduced pressure, whereby the title compound (130 mg, 18%) was obtained as a white solid.
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