Cl.O[CH2:3][C:4]1[N:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]2=[N:6][CH:5]=1.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1)([O-:15])=[O:14].[OH-].[Na+]>C(O)(=O)C.Cl>[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22][CH2:3][C:4]2[N:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]3=[N:6][CH:5]=2)=[CH:18][CH:17]=1)([O-:15])=[O:14]
A mixture of 3-hydroxymethylimidazo[1,2-a]pyridine hydrochloride (0.50 g) and 4-nitrothiophenol (0.42 g) in acetic acid (10 ml) and concentrated hydrochloric acid (10 ml) was stirred for 5 hours at 100° C. The reaction solution was cooled to 0° C., 8N aqueous solution of sodium hydroxide was added dropwise to adjust pH to 8. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The precipitated crystals were collected by filtration. The crystals were washed with diisopropyl ether, to give 3-(4-nitrophenylthiomethyl) imidazo[1,2-a]pyridine (0.54 g) as yellow crystals.
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