Preparation method of clausenamide intermediate
A kind of wampin amide and intermediate technology, applied in the field of medicine and chemical industry, can solve the problems of low yield, incomplete reaction, product ring breakage and the like, and achieve the effects of high reaction yield, less solvent consumption and convenient post-processing
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Embodiment 1
[0040] Embodiment 1 (comparative embodiment)
[0041] Preparation of N-methyl-N-phenacyl-3-phenyl glycidyl amide (KMnO 4 ·CuSO 4 Law)
[0042] Add 20g (0.067mol) of N-methyl-N-(2-hydroxy-2-phenyl)ethyl-3-phenylglycidylamide and 500ml of dichloromethane into a 1000ml single-necked bottle, heat slightly to completely dissolve the solid . After cooling to room temperature, add anhydrous CuSO 4 14.4g (0.09mol) and KMnO 4 42.4g (0.266mol, above 200 mesh). After stirring for 2 hours, the reaction was complete by TLC. Filter with diatomaceous earth, and wash with 500ml of dichloromethane for several times, until the washing solution shows only faint product spots on TLC. The filtrate and washings were combined, concentrated under reduced pressure to dryness to obtain about 12 g of light yellow oil. Treat the oily substance with 100ml of ether, stir until the oily substance is completely broken, and a white solid precipitates out. Cool to +3°C, collect the solid by filtration,...
Embodiment 2
[0043] Embodiment 2 (comparative embodiment)
[0044] Large-scale preparation of N-methyl-N-phenacyl-3-phenylglyceramide (KMnO 4 ·CuSO 4 Law)
[0045] Put 20kg of compound (I) into a 1000L reactor, suck in 670kg of dichloromethane, heat slightly to dissolve the solid completely, add 14.4kg of anhydrous copper sulfate and 42.4kg of potassium permanganate after cooling to room temperature. Stir the reaction at room temperature. Spot the plate after 10 hours to detect that the reaction is complete, centrifuge, and rinse the filter cake with dichloromethane repeatedly until the filtrate TLC detects that the fluorescence of the product is weak. The filtrates were combined and concentrated to dryness under reduced pressure to obtain 10 kg of yellow oil.
[0046] Stir the oily product with 50 L of diethyl ether to precipitate a solid under freezing conditions, put it in a freezer overnight, filter it with suction, and wash the solid with frozen diethyl ether to obtain 8.5 kg of a ...
Embodiment 3
[0048] Preparation of N-methyl-N-phenacyl-3-phenylglycidylamide (NCS-TEMPO method)
[0049] Dissolve 30 g (0.1 mol) of the raw material N-methyl-N-(2-hydroxy-2-phenyl) ethyl-3-phenyl glycidyl amide in 600 ml of dichloromethane, and add N-chlorobutyl at room temperature Diimide (NCS) 26.7g (0.2mol), after stirring for 10 minutes, the temperature was lowered to 0°C, and then 0.5g (3.2mmol) of TEMPO was added. After the addition, the mixture was stirred and raised to room temperature, and reacted for 5 hours, and the reaction was incomplete as detected by TLC. Cool down to 0°C again, add 0.5g (3.2mmol) of TEMPO and 13.3g (0.1mol) of NCS, raise the temperature to room temperature and stir for 5 hours, TLC shows that the reaction is complete. Filter with diatomaceous earth, and wash the filter cake with 400 ml of dichloromethane. The combined filtrate and washings were washed with saturated NaHCO 3 300ml, washed with 300ml of 1N HCl and 300ml of saturated brine, and dried over a...
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