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Synthesis method of 2-methyl-3,4-binitro-5-(methoxyphenyl) pyrazole

A technology of methoxyphenyl and synthesis method, which is applied in the synthesis field of 2-methyl-3,4-dinitro-5-pyrazole, can solve the problems of poor thermal stability, easy thermal decomposition and the like, and achieves thermal stability Sex-enhancing effect

Inactive Publication Date: 2016-01-20
丁玉琴
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The technical problem mainly solved by the present invention: Aiming at the problem that the traditional pyrazole compounds containing nitro and benzene rings have poor thermal stability and are easy to be decomposed by heating, a method of heating with methyl p-methoxybenzoate and toluene in a water bath is provided. React in sodium hydride, add acetonitrile dropwise to prepare 3-carbonyl-3-p-methoxyphenylpropionitrile, and then prepare 1-methyl-3,4 by reacting glacial acetic acid with iodine element and sulfuric acid solution containing iodic acid ,5-triiodopyrazole, then nitrate 1-methyl-3,4,5-triiodopyrazole to prepare 1-methyl-3,4,5-trinitropyrazole, and finally 1- Methyl-3,4,5-trinitropyrazole reacted with 3-carbonyl-3-p-methoxyphenylpropionitrile in water bath, and 2-methyl-3,4-di Nitro-5-(methoxyphenyl)pyrazole, which greatly improves the thermal stability of pyrazole compounds containing nitro and benzene rings

Method used

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  • Synthesis method of 2-methyl-3,4-binitro-5-(methoxyphenyl) pyrazole

Examples

Experimental program
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Effect test

example 1

[0019] Add 16g of methyl p-methoxybenzoate and 80mL of toluene in a 250mL round-bottomed three-necked flask, and then fully stir until methyl p-methoxybenzoate is completely dissolved. After adding 6g of 0.2mol sodium hydride, place it in a water bath Heat to 70°C, and at the same time add 10mL of 0.25mol / L acetonitrile solution dropwise to the three-necked flask, while controlling the dropping time to ensure that the dropwise addition is completed within 2 hours; after the dropwise addition is completed, heat it up to 90°C and continue stirring React for 20 hours, after the yellow substance is formed, detect the reaction by thin layer chromatography, after the completion of the detection reaction by thin layer chromatography, suction filter it, collect the yellow precipitate for the first time, and slowly stir the filtrate, add 20mL of glacial acetic acid, after cooling to 20°C, add 100mL of ice water, filter again to collect the filter cake and combine with the first yellow...

example 2

[0021] Add 16.5g of methyl p-methoxybenzoate and 81mL of toluene in a 250mL round-bottomed three-neck flask, then fully stir until methyl p-methoxybenzoate is completely dissolved, after adding 0.2mol sodium hydride of 6.5g, to Heat it in a water bath to 72°C, and at the same time add 11mL of 0.25mol / L acetonitrile solution dropwise to the three-necked flask, while controlling the dropping time to ensure that the dropwise addition is completed within 2 hours; after the dropwise addition is completed, heat it up to 90°C , continue stirring and reacting for 21h, after a yellow substance is generated, detect the reaction by thin-layer chromatography, after the completion of the detection reaction by thin-layer chromatography, suction filter it, collect the yellow precipitate for the first time, and slowly stir the filtrate 21mL of glacial acetic acid was added, and after it was cooled to 25°C, 102mL of ice water was added, and the filter cake was collected by suction filtration ...

example 3

[0023] Add 17g of methyl p-methoxybenzoate and 82mL of toluene to a 250mL round-bottomed three-necked flask, and then fully stir until methyl p-methoxybenzoate is completely dissolved. After adding 7g of 0.2mol sodium hydride, place it in a water bath Heat to 75°C, and add 12mL of 0.25mol / L acetonitrile solution dropwise to the three-necked flask at the same time, while controlling the dropping time to ensure that the dropwise addition is completed within 2 hours; after the dropwise addition is completed, heat it up to 90°C and continue Stir the reaction for 22 hours. After a yellow substance is generated, detect the reaction by thin-layer chromatography. After the detection reaction by thin-layer chromatography is completed, perform suction filtration to collect the first yellow precipitate, and slowly stir the filtrate. Add 22mL of glacial acetic acid, after cooling to 30°C, add 105mL of ice water, filter the filter cake again and combine it with the first yellow precipitate...

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Abstract

The invention relates to 2-methyl-3,4-binitro-5-(methoxyphenyl) pyrazole, and belongs to the field of chemical synthesis. By aiming at the problems that the conventional pyrazole compound containing nitryl and benzene rings has poor heat stability and can be easily thermally decomposed, the method adopts the technical scheme that methyl p-methoxybenzoate and methylbenzene are subjected to water bath heating to take reaction with sodium hydride; meanwhile, acetonitrile is dripped for preparing 3-carbonyl-p-methoxyphenyl propionitrile; then, through the reaction of the glacial acetic acid, the iodine and the sulfuric acid solution containing iodic acid, 1-methyl-3,4,5-tniodide pyrazole is prepared; then, the 1-methyl-3,4,5-tniodide pyrazole is subjected to nitrification to prepare 1-methyl-3,4,5-trinitro pyrazole; finally, the 1-methyl-3,4,5-trinitro pyrazole and the 3-methyl-3,4-binitro-5-(methoxyphenyl) pyrazole are subjected to water bath heating reaction; the 2-methyl-3,4-binitro-5-(methoxyphenyl) pyrazole is prepared and obtained through thin layer chromatographic reaction detection. Compared with an ordinary pyrazole compound containing nitryl and benzene rings, the 2-methyl-3,4-binitro-5-(methoxyphenyl) pyrazole has the advantage that the thermal stability is improved by 50 to 60 percent.

Description

technical field [0001] The invention relates to a synthesis method of 2-methyl-3,4-dinitro-5-(methoxyphenyl)pyrazole, which belongs to the field of chemical synthesis. Background technique [0002] In contemporary drug development, the research on heterocyclic compounds has become one of the hot spots in the field of new drug development. [0003] In the past ten years, more than 90% of the declarations of world drug patents are related to heterocyclic compounds. Among heterocyclic compounds, nitrogen-containing heterocycles are the most important, and among nitrogen-containing heterocyclic compounds, pyrazole compounds are one of the most rapidly developing fields in recent years. Since the 1, 3, 4, and 5- four positions of the pyrazole ring can undergo group transformation, this feature makes the types of pyrazole compounds diverse, so there are also many types of substituted pyrazole compounds with biological activity. Pyrazole compounds containing both amino and benzen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/16
CPCC07D231/16
Inventor 丁玉琴高力群
Owner 丁玉琴
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