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Synthetic method for N-substituent-3-aminoacrolein
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A technology for the synthesis of aminoacrolein, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as limiting industrial applications, and achieve high yields
Pending Publication Date: 2017-05-10
ZHEJIANG UNIV OF TECH
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However, this method uses highly toxic propynylalcohol, which limits its industrial application
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Embodiment 1
[0026] Synthesis of N,N-di-n-propyl-3-aminopropional
[0027] Add 11.5g (0.125mol) of 3-chloropropenol and 12.63g (0.125mol) of di-n-propylamine into a 500mL autoclave, then add 22.8g (0.15mol) of DBU, 4.35g (0.05mol) of γ-form manganese dioxide and 150 mL methanol. Raise the temperature to 60°C, turn on the mechanical stirring and feed air to make the pressure to 2.0MPa, then adjust the output of the air to 150mL / min, keep the temperature for 10h, and track and monitor the reaction progress with gas chromatography until the end of the reaction, and the reaction solution is cooled to room temperature ( 20°C), release the pressure, filter with suction, and precipitate the filtrate under reduced pressure to obtain the crude product of N,N-di-n-propyl-3-aminopropynaldehyde, and finally collect the components in the range of 125-130°C by vacuum distillation to obtain 18.83g yellow Liquid, yield 97.2%, purity 99.0%.
[0028] MS m / z (%): 155 (M + ,100.0),138(38.0),112(19.0),70(62...
Embodiment 1～30
[0030] Synthesis of N,N-di-n-propyl-3-aminopropional
[0031] The experimental operation was the same as that in Example 1, but the catalyst type, reaction temperature, reaction time, feed ratio, acid-binding agent type, reaction pressure, solvent consumption and other conditions were changed. The obtained results are shown in Table 1 (Examples 1-30).
[0032] Table 1 Synthesis of N,N-diisopropyl-3-aminopropional
[0033]
[0034]
Embodiment 31～36
[0036] The experimental operation was the same as in Example 1, and the substituents on the secondary amine were changed under the condition that other conditions remained unchanged, and the obtained results are shown in Table 2 (Examples 31-36).
[0037] Table 2 Synthesis of N-substituent-3-aminopropional
[0038]
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Abstract
The invention discloses a synthetic method for N-substituent-3-aminoacrolein. The method comprises the following steps: with secondary amine and 3-chloroallyl alcohol as raw materials, and active manganese dioxide as a catalyst, carrying out introducing into an air environment, then carrying out a reaction at 0.5 to 2.5 MPa and 40 to 90 DEG C for 6 to 14 h, and after completion of the reaction, postprocessing a reaction solution so as to obtain an N-substituent-3-aminoacrolein derivative, wherein the yield is 68% to 97%. Compared with a conventional method for synthesizing the N-substituent-3-aminoacrolein, the method provided by the invention has the advantages of low toxicity, low pollution, simple operation, etc.
Description
technical field [0001] The invention relates to a synthesis method of N-substituent-3-aminoacrolein. Background technique [0002] N-substituent-3-aminoacrolein is an important pharmaceutical and pesticide intermediate. It mainly has the following two types of synthesis methods: [0003] 1. N-substituted formamide, N-substituted secondary amine reacts with phosgene, oxalyl chloride, phosphorus oxychloride and bis(trichloromethyl)carbonate to generate Vilsmerier reagent, and then adds vinyl ether to heat the reaction to obtain The solution is then hydrolyzed under alkaline conditions to obtain N-substituent-3-aminoacrolein. For example, DE19825200 and US3974159 use N,N-dimethylformamide, phosgene and vinyl ether as raw materials to prepare N,N-dimethyl-3-aminoacrolein; EP0363934 reports N-formaldehyde under nitrogen protection N-methyl-N-phenyl-3-aminoacrolein was synthesized from oxalyl anilide, oxalyl chloride and vinyl ether; US5118853 and US2004229958 reported that N, ...
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