Cyanamide → (1-[6-[Pentafluoroethyl]pyridin-3-yl]ethyl)(methyl)-lambda4-sulfanylidenecyanamide

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To a stirred solution of the 5-(1-methylthioethyl)-2-pentafluoro-ethylpyridine (A) (0.16 g, 0.6 mmol) and cyanamide (0.025 g, 0.6 mmol) in THF (3 mL) cooled to 0° C. was added iodobenzene diacetate (0.19 g, 0.6 mmol) in one portion and the resulting mixture was stirred at 0° C. for 2 h and then at room temperature overnight. The solvent was removed in vacuo and the resulting mixture was suspended in brine-saturated NaHCO3 (9:1), which was then extracted with CH2Cl2-EtOAc (1:1, v/v) two times. The combined organic layer was dried over Na2SO4, filtered, concentrated, and dried to give 0.16 g of (1-{6-[pentafluoroethyl]pyridin-3-yl}ethyl)(methyl)-λ4-sulfanylidenecyanamide (B) as a brownish oil in 85% yield. LC-MS: mass calcd for C11H10F5N3S [M]+ 311.28. Found [M−1]+ 309.84

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