反应详情

To a mixture of 2-cyano-3-thiophen-2-yl-thioacrylamide (6.3 g, 33 mmol), 2-oxocyclopentaneacetic acid (4.6 g, 33 mmol) in 70 ml of ethanol was added N-methylmorpholine (6.6 g, 65 mmol). The resulting mixture was refluxed overnight, then 2-chloroacetamide (6.1 g, 65 mmol) and anhydrous potassium carbonate (9.0 g, 65 mmol) was added with stirring. The reaction mixture was continued to reflux overnight. The reaction mixture was cooled to room temperature and the solid was filtered and washed with ethanol. The sodium salt of product was dissolved in 100 ml of water and neutralized with 10% hydrochloric acid to pH<6. The precipitate was filtered and washed with water to give 3.7 g (31%) of pure product as a yellow solid. 1H-NMR (300 MHz, DMSO-d6): δ 12.24 (brs, 1H), 7.87 (d, J=5.1 Hz, 1H), 7.27-7.24 (m, 2H), 7.18 (brs, 2H), 5.93 (brs, 2H), 3.55 (m, 1H), 2.94 (dd, J=3.9, 16.2 Hz, 1H), 2.68 (m, 2H), 2.40 (m, 2H), 1.75 (m, 1H). ES MS m/z 374 (M+H)+, 372 (M−H)−.

1. temperatureThe resulting mixture was refluxed overnight
2. temperatureto reflux overnight
3. filtrationthe solid was filtered
4. washwashed with ethanol
5. dissolutionThe sodium salt of product was dissolved in 100 ml of water and neutralized with 10% hydrochloric acid to pH<6
6. filtrationThe precipitate was filtered
7. washwashed with water