Bromide ion → 2,2'-Thiodipyridine

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2.22 g of 2-mercaptopyridine and 0.96 g of 50% sodium hydride were dissolved in 50 ml of dimethylformamide, and the mixture was stirred at room temperature for one hour. Thereafter, 13.0 g of polyprenyl bromide of general formula (II) in which n=15 and A=Br were added. After the addition, the mixture was stirred overnight at room temperature. The reaction mixture was poured into about 50 ml of water and extracted with diethyl ether. The diethyl ether layer was washed with water and dried over anhydrous magnesium sulfate. The ether was distilled off to give a yellow liquid. The liquid was purified by silica gel column chromatography using hexane-ethyl acetate as the eluent to give 7.8 g of a slightly yellow liquid. NMR analysis of this liquid demonstrated that the signal (doublet, δ=3.91) assignable to --CH2Br of the starting polyprenyl bromide had disappeared and a signal (doublet, δ=3.78) assignable to --CH2S and a signal (multiplet, δ=6.75-8.35) assignable to --S--C5H4N had newly appeared. FD-MASS of this liquid gave m/e=1335.

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