反应详情

To a solution of N-benzylethane-1,2-diamine (3.00 g, 19.96 mmol) in anhydrous dioxane (15 mL) was added dimethyl cyanocarbonimidodithioate (3.50 g, 23.96 mmol). The mixture was refluxed for 16 hours, then diluted with dichloromethane (200 mL), washed with water (200 mL) and brine (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with ethyl acetate/hexane (1/4) to afford the title compound as a colorless solid in 95% yield (3.88 g): mp 120-122° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.36-7.22 (m, 5H), 6.86 (br s, 1H), 4.38 (s, 2H), 3.58-3.52 (m, 2H), 3.44-3.88 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 164.0, 135.5, 128.8, 128.1, 127.9, 119.4, 48.3, 46.1, 40.2; MS (ES+) m/z 201.2 (M+1).

1. temperatureThe mixture was refluxed for 16 hours
2. washwashed with water (200 mL) and brine (100 mL)
3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue was purified by column chromatography
7. washeluted with ethyl acetate/hexane (1/4)