Preparation method of 3-(4-methoxyphenylthio)-1-methyl-1H-pyrrolyl-2,5-dione compound

A technology of methoxyphenylthio and methoxythiophenol, applied in the field of pharmaceutical intermediates and their preparation, can solve the problems of high price, excessively long reaction route, many by-products, etc., and achieves easy industrial production and reaction Simple operation and the effect of shortening the reaction time

Inactive Publication Date: 2016-09-21
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Above-mentioned two kinds of synthetic methods all have the shortcoming such as too long reaction route, many by-products, low yield, meanwhile, the raw material used in the second method is difficult to obtain, expensive, increases production cost
Therefore, neither method is suitable for large-scale synthesis

Method used

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  • Preparation method of 3-(4-methoxyphenylthio)-1-methyl-1H-pyrrolyl-2,5-dione compound
  • Preparation method of 3-(4-methoxyphenylthio)-1-methyl-1H-pyrrolyl-2,5-dione compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Take 14.0g (0.1mol) of 4-methoxythiophenol, 11.1g (0.1mol) of N-methylmaleimide, 1.90g (0.01mol) of cuprous iodide, and fluoboric acid (content 40%) Add 21.9g (0.1mol) into a 250mL round bottom flask, then add 100mL of DMSO, heat to 120°C and stir for 8h, after the reaction is complete, add 50mL of water, stir for 5 minutes, extract with ethyl acetate 300mL×3, and use anhydrous sodium sulfate for the organic phase After drying, the solvent was evaporated, and the obtained solid was recrystallized with 95% ethanol to obtain 16.0 g of yellow solid 3-(4-methoxyphenylthio)-1-methyl-1H-pyrrole-2,5-dione, yield 64.5%, mp: 96-98°C.

Embodiment 2

[0040] Take 35.0g (0.25mol) of 4-methoxythiophenol, 33.3g (0.30mol) of N-methylmaleimide, 13.3g (0.07mol) of cuprous iodide, and fluoboric acid (content 40%) Add 55.0g (0.25mol) to a 500mL round bottom flask, then add DMSO 200mL, heat to 150°C and stir for 8h, after the reaction is complete, add 200mL of water, stir for 5 minutes, extract with 500mL×3 ethyl acetate, and use anhydrous sulfuric acid for the organic phase The sodium was dried, the solvent was evaporated, and the obtained solid was recrystallized with 95% ethanol to obtain 53.8 g of a yellow solid 3-(4-methoxyphenylthio)-1-methyl-1H-pyrrole-2,5-dione. Rate 86.5%, mp: 95~97℃.

Embodiment 3

[0042]Take 10.5g (0.075mol) of 4-methoxythiophenol, 16.6g (0.15mol) of N-methylmaleimide, 14.2g (0.075mol) of cuprous iodide, and fluoboric acid (content 40%) Add 33.0g (0.15mol) into a 250mL round bottom flask, then add 120mL dimethylacetamide, heat to 120°C and stir for 8h, after the reaction is complete, add 100mL of water, stir for 5 minutes, extract with 150mL×3 ethyl acetate, organic phase Dry with anhydrous sodium sulfate, evaporate the solvent, and recrystallize the obtained solid with 95% ethanol to obtain a yellow solid 3-(4-methoxyphenylthio)-1-methyl-1H-pyrrole-2,5-dione 13.6g, yield 73.1%, mp: 96~99℃

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Abstract

The invention relates to a preparation method of a 3-(4-methoxyphenylthio)-1-methyl-1H-pyrrolyl-2,5-dione compound. The 3-(4-methoxyphenylthio)-1-methyl-1H-pyrrolyl-2,5-dione compound has the structural formula shown in the description. The preparation method comprises the following steps: adding 4-methoxythiophenol, N-methylmaleimide, a copper salt catalyst and an additive into a reaction solvent, heating to 25-180 DEG C, enabling reaction for 4-24 hours and then purifying to obtain the 3-(4-methoxyphenylthio)-1-methyl-1H-pyrrolyl-2,5-dione compound. The 3-(4-methoxyphenylthio)-1-methyl-1H-pyrrolyl-2,5-dione compound prepared by the preparation method provided by the invention is high in yield, simple in reaction operation, short in reaction route, less in generation of waste gas, waste liquid and waste solid and easy to achieve industrial production.

Description

technical field [0001] The invention belongs to the field of pharmaceutical intermediates and preparation thereof, in particular to a preparation method of 3-(4-methoxyphenylthio)-1-methyl-1H-pyrrole-2,5-dione compound. Background technique [0002] 3-(4-Methoxyphenylsulfanyl)-1-methyl-1H-pyrrole-2,5-dione (I) and its derivatives are important drug synthesis intermediates, and have a wide range of antibacterial, Antifungal activity, especially to Gram-positive bacteria (such as: Bacillus subtilis, Staphylococcus aureus, etc.) J. Ind. Microbiol. Biot. 1992, 9(2), 91-96 and Igarashi, Y.; Watanabe, S. Investigation of quantitative structure antimicrobial activity relationship of 2-arylthio-N-methylmaleimides. Nippon. Kagaku. Kaishi, 1993 , 10, 1198-1200). According to literature reports, the synthesis methods of 3-(4-methoxyphenylthio)-1-methyl-1H-pyrrole-2,5-dione compounds mainly include two methods: method one is 4-methoxyphenylthio Nucleophilic addition reaction of pheno...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/456
CPCC07D207/456
Inventor 赵圣印杨振华张贺辉
Owner DONGHUA UNIV
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