Synthesis method of 3-ethoxy-N-p-tolyl propionamide

A technology of tolylpropionamide and tolylacrylamide, which is applied in the field of synthesis of 3-ethoxy-N-p-tolylpropionamide, can solve problems such as difficult separation and recovery, pollution of the atmospheric environment, and large environmental impact, and achieve product Good purity, high selectivity, and easy recovery

Active Publication Date: 2020-05-15
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the heating of dichloromethane will produce toxic gas, pollute the atmosphere, and also bring danger to the operator; and the yield is low, and the total yield is about 30%.
The second method uses N-p-tolylacrylamide and ethanol as raw materials, the reaction solvent is ethanol, and the catalyzer is copper chloride. It also needs to add a strong base such as NaOH, etc., and also needs to add cesium carbonate (Cs 2 CO 3 ), the post-treatment obtains 3-ethoxy-N-p-tolylpropionamide; the disadvantage of this method is that it needs to use a strong base, and the catalyst is dissolved in ethanol and is difficult to separate and recover, and the total yield of the target product is only 60%. , the yield is low, and a large amount of waste liquid is produced, which has a great impact on the environment

Method used

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  • Synthesis method of 3-ethoxy-N-p-tolyl propionamide
  • Synthesis method of 3-ethoxy-N-p-tolyl propionamide
  • Synthesis method of 3-ethoxy-N-p-tolyl propionamide

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Experimental program
Comparison scheme
Effect test

specific Embodiment 1

[0021] Add catalyst BaO (0.015g), N-p-tolylacrylamide (0.1mmol, 0.0161g), potassium fluoride (0.3mmol, 0.017g) and 3mL of ethanol into a 10mL reaction tube in sequence, and the reaction temperature is controlled at 90 ℃, and stirred for 5h. After the reaction is over, cool to room temperature, centrifuge the reaction system, take the supernatant liquid, and distill under reduced pressure (normal conditions: temperature 40°C, vacuum degree: -0.1MPa) to obtain 3-ethoxy-N -P-tolyl propionamide.

[0022] 1 HNMR(500MHz, CDCl 3 )δ8.47(s,1H),7.41(d,J=8.0Hz,2H), 7.13(d,J=7.9Hz,2H), 3.77(t,J=5.6Hz,2H), 3.61(q, J = 6.9Hz, 2H), 2.64 (t, J = 5.5Hz, 2H), 2.32 (s, 3H), 1.29 (t, J = 7.0Hz, 4H).

[0023] The equation involved in the reaction is as follows:

[0024]

specific Embodiment 2

[0026] Add the catalyst La to the 10mL reaction tube sequentially 2 O 3 (0.015g), N-p-tolylacrylamide (0.1mmol, 0.0161g), potassium fluoride (0.3mmol, 0.017g) and 3mL of ethanol, the reaction temperature was controlled at 90°C, and the reaction was stirred for 5h. After the reaction is finished, cool to room temperature, centrifuge the reaction system, take the supernatant liquid, and distill under reduced pressure to obtain 3-ethoxy-N-p-tolylpropionamide.

[0027] The equation involved in the reaction is as follows:

[0028]

specific Embodiment 3

[0030] Add the catalyst CeO sequentially to the 10mL reaction tube 2 (0.015g), N-p-tolylacrylamide (0.1mmol, 0.0161g), potassium fluoride (0.3mmol, 0.017g) and 3mL of ethanol, the reaction temperature was controlled at 90°C, and the reaction was stirred for 5h. After the reaction is completed, cool to room temperature, centrifuge the reaction system, take the supernatant liquid, and distill under reduced pressure to obtain 3-ethoxy-N-p-tolylpropionamide.

[0031] The equation involved in the reaction is as follows:

[0032]

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Abstract

The invention relates to the technical field of fine chemical engineering, and discloses a synthetic method of 3-ethoxy-N-p-tolyl propionamide. The preparation method comprises the specific steps: adding N-p-tolyl acrylamide, potassium fluoride and a metal oxide catalyst into a certain amount of ethanol, and heating and stirring to react, and thus obtaining 3-ethoxy-N-p-tolyl propionamide. Compared with an existing synthesis method, the method does not need to introduce a strong acid or strong alkali reagent, has the advantages of high yield, simple operation and small influence on the environment, has potential industrial value, and is worthy of popularization and application.

Description

Technical field [0001] The invention belongs to the field of fine chemicals and relates to a method for synthesizing 3-ethoxy-N-p-tolylpropionamide. Background technique [0002] Compounds containing carbon-oxygen bonds are widely present in chemical substances and biologically active molecules. The carbon atoms in the positive charge center are easily attacked by nucleophiles and undergo nucleophilic substitution reactions. Therefore, such compounds are valuable intermediates in organic synthesis. , Can be used as a starting point for further reaction (domino reaction) or can be protonated to obtain β-hydroxycarbonyl (or carboxyl) compound. Take 3-ethoxy-N-p-tolylpropionamide as an example. As an intermediate, it can be used in the synthesis of medicines, pesticides, and dye chemicals, and has received widespread attention. At present, there are two common methods for synthesizing 3-ethoxy-N-p-tolylpropionamide: the first method involves the reaction of N-p-tolylacrylamide with...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C235/16
CPCC07C231/12C07C235/16
Inventor 张磊傅雯倩唐天地吴蒙雨张原何建政
Owner CHANGZHOU UNIV
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