[CH3:1][S:2][CH:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([Cl:14])([Cl:13])[Cl:12])=[N:9][CH:10]=1)[CH3:4].[N:15]#[C:16][NH2:17].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C1COCC1>[Cl:12][C:11]([Cl:14])([Cl:13])[C:8]1[N:9]=[CH:10][C:5]([CH:3]([S:2]([CH3:1])=[N:17][C:16]#[N:15])[CH3:4])=[CH:6][CH:7]=1To a stirred solution of 5-[1-(methylthio)ethyl]-2-(trichloromethyl)-pyridine (B) (0.55 g, 2.3 mmol) and cyanamide (0.097 g, 2.3 mmol) in THF (7 mL) cooled to 0° C. was added iodobenzene diacetate (0.75 g, 2.3 mmol) in one portion. The resulting mixture was stirred at 0° C. for 1 hr and then at room temperature for 2 hr. The solvent was removed in vacuo and the resulting mixture was purified on silica gel using 50% acetone in hexane (v/v) to give 0.254 g of {1-[6-(trichloromethyl)pyridin-3-yl]ethyl}(methyl)-λ4-sulfanylidenecyanamide (3) as an off-white solid in 40% yield. 1H NMR for the diastereomeric mixture (300 MHz, d6-acetone) δ 8.87 (s, 1H), 8.21-8.25 (m, 2H), 4.65-4.76 (m, 1H), 2.86-2.66 (m, 3H), 1.88-1.92 (m, 3H).
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