Bromide ion → 2,2'-Thiodipyridine

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1.11 g of 2-mercaptopyridine and 0.48 g of 50% sodium hydride were dissolved in 25 ml of dimethyl formamide, and the mixture was stirred at room temperature for 1 hour. A solution of 6.5 g of polyprenyl bromide of general formula (II) in which n is 15 and A2 is Br in 5 ml of N,N-dimethylformimide was added dropwise. 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. Then, 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 an eluent to give 3.9 g of a slightly yellow liquid. The NMR analysis of this liquid showed that the signal (doublet, δ=3.91) assigned to --CH2Br of the starting polyprenyl bromide disappeared, and a signal (doublet, δ=3.78) assigned to --CH2S and a signal (multiplet, δ=6.75-8.35) assigned to --S--C5H4N newly appeared. The FD-MASS analysis of this liquid gave m/e=1335.

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