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A kind of method utilizing microchannel reaction device to prepare deuterated aniline compounds

A technology of aniline compounds and microchannel reaction, which is applied in the preparation of amino compounds from amines, the preparation of organic compounds, organic chemical methods, etc., can solve the problems of large amount of heavy water usage, incomplete deuterium, long reaction time, etc., to achieve Reduced usage of heavy water, high deuterium rate, shortened reaction time

Active Publication Date: 2020-04-07
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The technical problem to be solved by the present invention provides a method for preparing deuterated aniline compounds, so as to solve the problems in the prior art such as large amount of heavy water used, too long reaction time, incomplete deuterated, high cost, etc.

Method used

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  • A kind of method utilizing microchannel reaction device to prepare deuterated aniline compounds
  • A kind of method utilizing microchannel reaction device to prepare deuterated aniline compounds
  • A kind of method utilizing microchannel reaction device to prepare deuterated aniline compounds

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Effect test

Embodiment 1

[0034] Weigh anthranilonitrile (1.0equiv, 4.0mmol), measure hydrochloric acid heavy aqueous solution (1.0equiv, 0.2M, 20.0mL) and place in a sealed conical flask for ultrasonic mixing for 30min; The solution was pushed into the microchannel reactor at a flow rate of 1.0 mL / min by a syringe pump after exhausting the air in the syringe, and the residence time was 4 min. The above-mentioned microchannel reactor is placed in a microwave field with an inner diameter of 0.5mm. The above reaction temperature is 180° C., and the reaction liquid is collected after the reaction is completed. The conversion rate was 99.3%, the deuteration rate was 99.4%, and the isolated yield was 97.3%.

Embodiment 2

[0036] Weigh aniline (1.0equiv, 4.0mmol), measure hydrochloric acid heavy aqueous solution (1.0equiv, 0.2M, 20.0mL) and place in a conical flask, seal and ultrasonically mix for 30min; The air in the syringe is then pushed into the microchannel reactor at a flow rate of 1.0 mL / min by a syringe pump, and the residence time is 4 min. The above-mentioned microchannel reactor is placed in a microwave field with an inner diameter of 0.5mm. The above reaction temperature is 180° C., and the reaction liquid is collected after the reaction is completed. The conversion rate was 95.7%, the deuteration rate was 83.1%, and the isolated yield was 82.8%.

Embodiment 3

[0038] Weigh m-chloroaniline (1.0equiv, 4.0mmol), measure hydrochloric acid heavy aqueous solution (1.0equiv, 0.2M, 20.0mL) and place in a sealed conical flask for ultrasonic mixing for 30min; use a syringe to extract the mixed solution after ultrasonic mixing, After exhausting the air in the syringe, push it into the microchannel reactor at a flow rate of 1.0 mL / min with a residence time of 4 min through a syringe pump. The above-mentioned microchannel reactor is placed in a microwave field with an inner diameter of 0.5mm. The above reaction temperature is 180° C., and the reaction liquid is collected after the reaction is completed. The conversion rate was 98.4%, the deuteration rate was 89.7%, and the isolated yield was 85.5%.

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Abstract

The invention discloses a method for preparing a d-phenylanine compound by using a microchannel reaction device. The method comprises the following steps: (1) mixing an aniline compound I, an acid and heavy water, implementing ultrasonic treatment evenly to obtain a mixed solution; and (2) pumping the mixed solution obtained in the step (1) into a microchannel reactor of the microchannel reaction device, reacting under the action of a microwave field or ultrasonic wave; and collecting a reaction liquid after finishing the reaction to obtain the d-phenylanine compound II. The method has the advantages of higher conversion rate, higher deuterium content, higher yield and reduction of the quantity of the heavy water used in the reaction. Therefore, the post-processing is simple, and a high-purity product is obtained.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for preparing deuterated aniline compounds using a microchannel reaction device. Background technique [0002] Aniline compound I is the important chemical raw material of industries such as pharmacy, dyestuff and textile. With the development of the chemical industry, the demand for aniline chemicals is on the rise. At present, more than 80,000 tons of aniline are produced in China every year, and there are more than 150 kinds of its downstream products, such as: acid bright yellow, golden light red, poisonous grass and so on. Therefore, in recent years, aniline compound I has been a hot spot of research scholars. [0003] In the research process, due to the high activity of the amino group, we often use aniline compound I as an intermediate in organic chemistry, and then chemically modify it to obtain the target compound. When we obtain an effective and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B59/00C07C253/30C07C255/58C07C209/68C07C211/46C07C211/52C07C211/47
CPCC07B59/001C07B2200/05C07C209/68C07C253/30C07C255/58C07C211/46C07C211/52C07C211/47
Inventor 郭凯郑明卫万力
Owner NANJING TECH UNIV
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