4-chloro(bromo)-5-alkylthio-3-pyrrolidone derivative and synthesis thereof
A technology of alkylthio and pyrrolidone, which is applied in the field of 4-chloro(bromo)-5-alkylthio-3-pyrrolone derivatives and synthesis thereof, and achieves the effects of low cost, easy industrial production and high yield
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Embodiment 1
[0029]
[0030] In the glove box, weigh 1-thiomethyl-1-anilino-5-phenyl-1,4-pentadien-3-one 2a (0.5mmol), copper chloride (2.0mmol), carbonic acid Potassium (2.0mmol), lithium chloride (1.5mmol) in a 25mL Schlenk reaction flask, under argon, add N,N-dimethylformamide (DMF) solvent 5mL, stir at room temperature for 2 minutes, put in 100 °C in an oil bath for 12 hours. After the reaction, the mixture was cooled to room temperature, filtered with diatomaceous earth, extracted with ethyl acetate and 10% ammonia water in mass concentration, collected the organic phase, dried over anhydrous magnesium sulfate, filtered, removed volatile components under reduced pressure, and then used a silica gel column to Chromatographic separation (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=20:1) gave the target product 1a as a red solid (115 mg, yield 70%). The target product was confirmed by NMR and high-resolution mass spectrometry.
Embodiment 2
[0032]
[0033] In the glove box, weigh 1-thiomethyl-1-p-methoxyanilino-5-phenyl-1,4-pentadien-3-one 2b (0.5 mmol), copper chloride (1.5 mmol), potassium phosphate (1.5mmol), and lithium chloride (1.5mmol) in a 25mL Schlenk reaction flask, under argon, add 5mL of DMF solvent, stir at room temperature for 2 minutes, and put it into an oil bath at 120°C for reaction 6 Hour. After the reaction, the mixture was cooled to room temperature, filtered with celite, extracted with ethyl acetate and 10% ammonia water, the organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the volatile components were removed under reduced pressure, followed by silica gel column chromatography Separation (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=20:1) gave the target product 1b (166 mg, yield 93%) as a red solid. The target product was confirmed by NMR and high-resolution mass spectrometry.
Embodiment 3
[0035]
[0036]In the glove box, successively weigh 1-thiomethyl-1-m-fluoroanilino-5-phenyl-1,4-pentadien-3-one 2c (0.5mmol), copper chloride (2.0mmol) , potassium phosphate (2.0mmol), and lithium chloride (1.5mmol) were placed in a 25mL Schlenk reaction flask, under argon, 5mL of DMF solvent was added, stirred at room temperature for 2 minutes, and placed in an oil bath at 80°C for 2 hours. After the reaction, the mixture was cooled to room temperature, filtered with celite, extracted with ethyl acetate and 10% ammonia water, the organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the volatile components were removed under reduced pressure, followed by silica gel column chromatography Separation (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=20:1) gave the target product 1c (159 mg, yield 92%) as a red solid. The target product was confirmed by NMR and high-resolution mass spectrometry.
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