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Synthesis method of 3-alkylmercapto-1-methyl-4-morpholinyl maleimide compound

A technology of methylmaleimide and maleimide, applied in the field of organic compound synthesis, can solve problems such as unstable pharmacological activity or biological activity research, achieve important social and economic significance, simple reaction conditions, The effect of high yield and purity

Active Publication Date: 2020-06-26
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Although the existing technology can solve the amine thiolation reaction of maleimide, the use of malodorous and unstable thiols as thiolation reagents in the reaction process limits the further industrial application of the reaction and the pharmacological activity or biological activity of molecular compounds. Activity research, using odorless and stable Buente's salt as a thiolation reagent has not been reported so far

Method used

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  • Synthesis method of 3-alkylmercapto-1-methyl-4-morpholinyl maleimide compound
  • Synthesis method of 3-alkylmercapto-1-methyl-4-morpholinyl maleimide compound
  • Synthesis method of 3-alkylmercapto-1-methyl-4-morpholinyl maleimide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of 3-(2-ethoxyethylmercapto)-1-methyl-4-morpholinomaleimide

[0033]

[0034] At room temperature, substituted 2-ethoxyethylmercapto Buente salt (0.6mmol, 3equiv), morpholine (0.4mmol, 2equiv), N-methylmaleimide (0.2mmol, 1equiv), iodine Cuprous chloride (0.02 mmol, 0.1 equiv) and 2 mL of 1,2-dichloroethane were added to the reaction tube, then filled with oxygen, and replaced three times, and stirred at a reaction temperature of 100° C. for 24 h. The reaction mixture was cooled, then diluted with ethyl acetate, filtered to a heart bottle, then the solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ether = 9: 1), and the product was a yellow solid. The melting point is 51-52° C., the yield is 95%, and the product weight is 57 mg.

[0035] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0036] 1 H NMR (500MHz, CDCl 3 ): δ4.20(t, J=4.70Hz, 4H), 3.79(t, J=4.7...

Embodiment 2

[0042] Synthesis of 3-decylmercapto-1-methyl-4-morpholinomaleimide

[0043]

[0044] At room temperature, substituted decylmercapto Buente salt (0.6mmol, 3equiv), morpholine (0.4mmol, 2equiv), N-methylmaleimide (0.2mmol, 1equiv), cuprous iodide (0.02 mmol, 0.1 equiv) and 2 mL of 1,2-dichloroethane were added to the reaction tube, then filled with oxygen, and replaced three times, and stirred at a reaction temperature of 100°C for 24h. The reaction mixture was cooled, then diluted with ethyl acetate, filtered to a heart bottle, then the solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ether = 9: 1), and the product was a yellow solid. The melting point is 49-50° C., the yield is 92%, and the product weight is 68 mg.

[0045] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0046] 1 H NMR (500MHz, CDCl 3 ): δ4.18(t, J=4.70Hz, 4H), 3.79(t, J=4.70Hz, 4H), 2.99(s, 3H), 2.70(t, J...

Embodiment 3

[0052] Synthesis of 3-butylmercapto-1-methyl-4-morpholinylmaleimide

[0053]

[0054] At room temperature, substituted butylmercapto Buendt's salt (0.6mmol, 3equiv), morpholine (0.4mmol, 2equiv), N-methylmaleimide (0.2mmol, 1equiv), cuprous iodide (0.02 mmol, 0.1 equiv) and 2 mL of 1,2-dichloroethane were added to the reaction tube, then filled with oxygen, and replaced three times, and stirred at a reaction temperature of 100°C for 24h. The reaction mixture was cooled, then diluted with ethyl acetate, filtered to a heart bottle, then the solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ether = 9: 1), the product was a yellow liquid, The yield is 88%, and the product weight is 50 mg.

[0055] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0056] 1 H NMR (500MHz, CDCl 3 ): δ4.19(t, J=4.70Hz, 4H), 3.79(t, J=4.70Hz, 4H), 2.99(s, 3H), 2.71(t, J=7.40Hz, 2H), 1.56-1.52 (m, 2...

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Abstract

The invention relates to a synthetic method of a 3-alkylmercapto-1-methyl-4-morpholinyl maleimide compound. The preparation method comprises: in an organic solvent, under the condition of oxygen, carrying out a cascade reaction catalyzed by transition metal copper by taking alkylmercapto Bunte salt, morpholine and N-methylmaleimide as reaction raw materials, so as to obtain the 3-alkylmercapto-1-methyl-4-morpholinyl maleimide compound. The method is simple in reaction condition and high in product yield and purity, opens up a synthetic route and method for preparation of the 3-alkylmercapto-1-methyl-4-morpholinyl maleimide compound, and has good application potential and research value.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of a 3-alkylmercapto-1-methyl-4-morpholino maleimide compound. Background technique [0002] As an important class of amide compounds, maleimide widely exists in natural products, bioactive molecules and clinical drug molecules, and the parent structure can also be prepared through various conversion reactions to succinimide, pyrrolidine, lactam Therefore, based on the application of maleimide compounds in different fields, how to efficiently and greenly synthesize derivatives with maleimide skeletons has always been the goal pursued by organic chemists. [0003] In 2002, Dubinina, G.G. et al. reported (Reactions of 3,4-dichloromaleimideswith N-and S-nucleophiles, Ukrainskii Khimicheskii Zhurnal, 68,47-51; 2002), utilizing 3,4-dichloromaleimides , arylamine and thiophenol are refluxed under the triethylamine condition to obtain 3...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/456
CPCC07D207/456Y02P20/584
Inventor 吴戈李佳马云飞
Owner WENZHOU MEDICAL UNIV
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