A kind of synthetic method of 6-chloroimidazo[1,2-b]pyridazine-3-carbonitrile
A synthetic method, 2-b technology, applied in the direction of organic chemistry, etc., can solve the problems of 6-chloroimidazole that has not been disclosed, complex steps of the preparation method, and difficult synthesis, and achieve the effects of easy acquisition, stable product quality, and convenient operation
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Embodiment 1
[0022] 50g (390mmol) of 3-amino-6-chloropyridazine is the reaction raw material, react with 400g N-dimethylformamide dimethyl acetal at 60°C for 4 hours, and the reaction is completed to obtain N,N-dimethyl -N'-3-(6-chloro-pyridazinyl)-formamidine intermediate, remove excess N,N-dimethylformamide dimethyl acetal by rotary evaporation, add DMF400ml and drop bromoacetonitrile (60.8g , 507mmol), reacted at 60°C for 10 hours, after the reaction was completed, cooled to room temperature, added an appropriate amount of saturated sodium bicarbonate solution, adjusted the pH to 7.9, stood for three hours, and precipitated solids, dissolved all the solids in 300ml of ethyl acetate , washed three times with water, 100ml each time, then washed twice with saturated brine, 100ml each time, then dried with anhydrous sodium sulfate, concentrated by rotary evaporation, mixed with n-hexane:ethyl acetate volume ratio of 1:2 The solution was recrystallized to obtain 58.1 g of pure product. The ...
Embodiment 2
[0024] 50g (390mmol) of 3-amino-6-chloropyridazine is the reaction raw material, react with 400g N-dimethylformamide dimethyl acetal at 110°C for 3 hours, and N,N-dimethyl -N'-3-(6-chloro-pyridazinyl)-formamidine intermediate, remove excess N,N-dimethylformamide dimethyl acetal by rotary evaporation, add DMF400ml and drop bromoacetonitrile (60.8g , 507mmol), reacted at 80°C for 8 hours, after the reaction was completed, cooled to room temperature, added an appropriate amount of saturated sodium bicarbonate solution, adjusted the pH to 8.3, stood for three hours, and precipitated solids, dissolved all the solids in 300ml of ethyl acetate , washed three times with water, 100ml each time, then washed twice with saturated brine, 100ml each time, then dried with anhydrous sodium sulfate, concentrated by rotary evaporation, mixed with n-hexane:ethyl acetate volume ratio of 1:2 The solution was recrystallized to obtain 55.5 g of pure product. The purity is 99.1%, and the yield is 79...
Embodiment 3
[0026] 50g (390mmol) of 3-amino-6-chloropyridazine is the reaction raw material, react with 400g N-dimethylformamide dimethyl acetal at 50°C for 8 hours, and N,N-dimethyl -N'-3-(6-chloro-pyridazinyl)-formamidine intermediate, remove excess N,N-dimethylformamide dimethyl acetal by rotary evaporation, add 400ml of acetonitrile and drop bromoacetonitrile (60.8 g, 507mmol), reacted at 100°C for 10 hours, after the reaction was completed, cooled to room temperature, added an appropriate amount of saturated sodium bicarbonate solution, adjusted the pH to 7.4, stood for three hours, and precipitated solids, dissolved all solids in 300ml ethyl acetate in water, washed three times with 100ml each time, then washed twice with saturated brine, 100ml each time, then dried with anhydrous sodium sulfate, concentrated by rotary evaporation, and the volume ratio of n-hexane:ethyl acetate was 1:2 The mixed solution was recrystallized to obtain 54.2 g of pure product. The purity is 98.5%, and ...
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