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Electrochemical synthesis method of 3,4-dibromomaleimide

A technology of dibromomaleimide and maleimide, applied in the field of electrochemical synthesis of 3,4-dibromomaleimide, which can solve the problems of high cost, harsh reaction conditions, and inconvenient operation

Active Publication Date: 2021-05-14
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, the organic synthesis methods for preparing 3,4-dibromomaleimide mostly have the following deficiencies: additional oxidants, metal catalysts are required, the reaction needs to be carried out step by step, the use of bromine sources with high cost or inconvenient operation, and harsh reaction conditions

Method used

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  • Electrochemical synthesis method of 3,4-dibromomaleimide
  • Electrochemical synthesis method of 3,4-dibromomaleimide
  • Electrochemical synthesis method of 3,4-dibromomaleimide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] The synthetic method of N-benzyl-3,4-dibromomaleimide is as follows:

[0074] In an H-type electrolytic cell (model: CH2001-S; manufacturer: Tianjin Aida Hengsheng Technology Development Co., Ltd.) equipped with a platinum plate (1cm×2cm) as the cathode electrode and the anode electrode, nafion117 is used as the cation exchange membrane. Add 1 mmol N-benzyl-maleimide, 6 mmol NaBr, 4 mmol LiClO to the anode chamber 4 , 20 mL DMF, 20 mL phosphate buffer (pH7~8). Add 4 mmol LiClO to the cathode chamber 4 , 40 mL ultrapure water. Reaction at room temperature, with 20 mA / cm 2 The current density is constant current reaction, the reaction temperature is 25°C, the reaction time is 21h, and the reaction is tracked by TLC. After the reaction, the reaction mixture in the anode chamber is taken out, and ethyl acetate is added for extraction, and the ethyl acetate solution layer is separated. , dried, concentrated, and the product N-benzyl-3,4-dibromomaleimide was isolated with...

Embodiment 2- Embodiment 10

[0078] The corresponding 3,4-dibromomaleimide was synthesized with different maleimide derivatives, and the experimental parameters and experimental steps were the same as in Example 1. Examples The experimental results are shown in Table 1.

[0079] Table 1 Synthesis of 3,4-dibromomaleimide from maleimide derivatives.

[0080]

[0081]

Embodiment 2

[0082] Product in Example 2 The hydrogen and carbon spectra of image 3 , Figure 4 As shown, the NMR data are as follows:

[0083] 1 H NMR (500 MHz, CDCl 3 ): δ4.01 (tt, J 1 =12.47Hz, J 2 =3.91Hz, 1H), 2.09-2.01(m,2H), 1.88-1.84(m,2H),1.73-1.67(m,3H), 1.38-1.18(m,3H); 13 C NMR (125MHz, CDCl 3 ) : δ163.73, 129.28, 52.82, 29.98, 25.84, 24.90.

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Abstract

The invention relates to the technical field of organic synthesis, in particular to an electrochemical synthesis method of 3,4-dibromomaleimide. The 3,4-dibromomaleimide is prepared in one pot in an anode chamber by taking maleimide as an initial raw material and taking a cheap, safe and easily available bromide as a bromine source. The method is simple to operate, green and friendly, the reaction condition is mild, the raw material is cheap and easily available, and the production cost can be effectively reduced. The electrochemical reaction is realized by obtaining and losing electrons from reactants on the electrode, and additional oxidizing agents and metal catalysts are not needed, so that the material consumption is reduced, and the environmental pollution is reduced; the reaction is carried out at normal temperature and normal pressure, which is very beneficial for saving energy and reducing equipment investment; the technological process is simple, the operation is simple and convenient, the reaction is easy to control, and the 3,4-dibromomaleimide can be obtained through one-pot reaction; the used bromide is cheap and easy to obtain, so that the raw material cost is reduced, and the use is very safe; and the reaction process is environment-friendly and meets the requirements of an environment-friendly chemical process.

Description

technical field [0001] The invention relates to the technical field of electrochemical synthesis, in particular to an electrochemical synthesis method of 3,4-dibromomaleimide. Background technique [0002] Maleimide is an important organic reaction intermediate. As a drug intermediate, maleimide is an excellent electrophile and dienophile, and is an important structural mother nucleus of a class of marine natural alkaloids and biologically active molecules. Bromomaleimide introduces a bromine atom with an electron-withdrawing effect on the basis of maleimide, which has better electrophilicity than maleimide, and is widely used in the synthesis of pharmaceutical intermediates. Applications. For example: N-methyl-3,4-dibromomaleimide is an important intermediate in the synthesis of indole maleimide. Pharmacological studies have shown that indole maleimide compounds such as Ruboxistau-fin, Enzastaurin and JTr-010 have biological activities such as anti-tumor, anti-bacterial ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/05C25B3/07C25B3/09C25B3/11C25B3/27
Inventor 陈万里赵婧朱英红褚有群
Owner ZHEJIANG UNIV OF TECH
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