Cl[C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([Cl:8])=[CH:6][N:7]=1.[C:11]1([SH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O.C(OCC)(=O)C>[Cl:8][C:5]1[N:4]=[C:3]([C:9]#[N:10])[C:2]([S:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][CH:6]=1In 50 mL of N,N-dimethylformamide was dissolved 10.0 g of 3,6-dichloro-2-pyrazinecarbonitrile. After adding 6.49 mL of thiophenol and 11.91 g of potassium carbonate successively, the mixture thus obtained was stirred at 40° C. for 3 hours. The reaction mixture was poured into a mixture of 100 mL of ethyl acetate and 100 mL of water, and pH was adjusted to 2 with 6 mol/L hydrochloric acid. The organic layer was separated, washed successively with water and saturated aqueous solution of sodium chloride, and dried on anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent: toluene:n-hexane=1:3] to obtain 3.80 g of 6-chloro-3-(phenylsulfanyl)-2-pyrazinecarbonitrile as a light yellow-colored oily product.
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