反应详情

To a mixture of thionyl chloride (3.7 g, 31 mmol) in toluene (10 ml) containing 3 drops of pyridine is added 4-bromomandelic acid (2.9 g, 13 mmol) in diethylether (40 ml). The reaction mixture is refluxed for 2 hours. The solvent is removed and the residue is co-evaporated with toluene. Subsequently the residue is dissolved in dioxane (20 ml) and added to 2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethylamine (2.2 g, 11 mmol) and triethylamine (1.0 g, 10 mmol) in dioxane (20 ml). The resulting mixture is stirred for 16 hours, diluted with water (100 ml) and extracted with ethyl acetate (2×200 ml). The combined organic layer is washed with brine (150 ml), dried over magnesium sulfate and evaporated. 2-(4-Bromo-phenyl)-2-chloro-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide is obtained which is purified by chromatography on silica gel using ethyl/acetate/hexane as eluent. 1H-NMR (300 MHz, CDCl3): 2.53(t, 1H, C≡CH), 2.82(t, 2H, CH2CH2), 3.60(t, 2H, CH2CH2), 3.87(s, 3H, OCH3), 4.79(d, 2H, OCH2), 5.29(s, 1H, CHCl), 6.70-7.48(m, 8H, CH arom., NH).

1. temperatureThe reaction mixture is refluxed for 2 hours
2. customThe solvent is removed
3. dissolutionSubsequently the residue is dissolved in dioxane (20 ml)
4. extractionextracted with ethyl acetate (2×200 ml)
5. washThe combined organic layer is washed with brine (150 ml)
6. dry with materialdried over magnesium sulfate
7. customevaporated