反応 #169513

反応方程式

5-[1-(methylthio)ethyl]-2-(trichloromethyl)-pyridine

5-[1-(methylthio)ethyl]-2-(trichloromethyl)pyridine

cyanamide

iodobenzene diacetate

→

(1E)-methyl{1-[6-(trichloromethyl)pyridin-3-yl]ethyl}-sulfanylidenecyanamide

収率 40.0%

溶媒

THF

反応条件

後処理

1. 1
   workup.WAITat room temperature for 2 hr
2. 2
   その他The solvent was removed in vacuo
3. 3
   その他the resulting mixture was purified on silica gel using 50 percent acetone in hexane

実験手順

To 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 percent acetone in hexane to give 0.254 g of (1E)-methyl{1-[6-(trichloromethyl)pyridin-3-yl]ethyl}-sulfanylidenecyanamide (C) as an off-white solid in 40 percent yield. 1H NMR for the diastereomeric mixture (300 MHz, ds-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).

出典