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Preparation method of 1-[(2-allylthio) formyl]-4-(2-methylphenyl)-5-amino-1H-pyrazole-3-ketone

A technology of propenyl thio and methyl phenyl, applied in the field of compound preparation, can solve the problems of low product yield and complicated process, and achieve the effects of high yield and simple process

Inactive Publication Date: 2022-03-15
山东广浦生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The object of the present invention is to propose a preparation method of 1-[(2-propenylthio)formyl]-4-(2-methylphenyl)-5-amino-1H-pyrazol-3-one, To solve the problems of complicated technical process and low product yield in the prior art

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  • Preparation method of 1-[(2-allylthio) formyl]-4-(2-methylphenyl)-5-amino-1H-pyrazole-3-ketone

Examples

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Comparison scheme
Effect test

Embodiment 1

[0042] A preparation method of 1-[(2-propenylthio)formyl]-4-(2-methylphenyl)-5-amino-1H-pyrazol-3-one, comprising the steps of:

[0043] Step 1, replace the air in the reactor with nitrogen, after the nitrogen replacement, add 225kg of water and 225kg of 5-amino-4-(2-methylphenyl)-1,2-dihydro to the reactor -3H-pyrazol-3-one, 438kg of methanol;

[0044] Step 2, stir and cool down to 7°C;

[0045] Step 3, add 167kg of 30% sodium hydroxide dropwise to the reactor, and adjust the pH to 11.5;

[0046] Step 4, after adjusting the pH value, add 400kg xylene, fully stir and dissolve;

[0047] Step 5, after dissolving, drop 700kg of S-allyl thiochloroformate, the temperature of the reactor is controlled at 0-15°C, with the dropwise addition of S-allyl thiochloroformate, When the pH value of the solution in the reaction kettle gradually drops from 11.0-12.25 to 10.0-10.9, 167kg of 30% sodium hydroxide is added dropwise again, and at this time, the double dropwise addition of S-allyl...

Embodiment 2

[0057] A preparation method of 1-[(2-propenylthio)formyl]-4-(2-methylphenyl)-5-amino-1H-pyrazol-3-one, comprising the steps of:

[0058] Step 1, replace the air in the reactor with nitrogen, after the nitrogen replacement, add 225kg of water and 225kg of 5-amino-4-(2-methylphenyl)-1,2-dihydro to the reactor -3H-pyrazol-3-one, 337.5kg of methanol;

[0059] Step 2, stir and cool down to 8°C;

[0060] Step 3, add 175kg of 30% sodium hydroxide dropwise to the reactor, and adjust the pH to 12;

[0061] Step 4, after adjusting the pH value, add 440kg xylene, fully stir and dissolve;

[0062] Step 5, after dissolving, dropwise add 735kg of S-allyl thiochloroformate, the temperature of the reactor is controlled at 0-15°C, with the dropwise addition of S-allyl thiochloroformate, When the pH value of the solution in the reaction kettle gradually drops from 11.0-12.25 to 10.0-10.9, 167kg of 30% sodium hydroxide is added dropwise again, and at this time, the double dropwise addition of...

Embodiment 3

[0072] A preparation method of 1-[(2-propenylthio)formyl]-4-(2-methylphenyl)-5-amino-1H-pyrazol-3-one, comprising the steps of:

[0073] Step 1, replace the air in the reactor with nitrogen, after the nitrogen replacement, add 225kg of water and 225kg of 5-amino-4-(2-methylphenyl)-1,2-dihydro to the reactor -3H-pyrazol-3-one, 435kg of methanol;

[0074] Step 2, stir and cool down to 8°C;

[0075] Step 3, add 190kg of 30% sodium hydroxide dropwise to the reactor, and adjust the pH to 12.25;

[0076] Step 4, after adjusting the pH value, add 360kg xylene, fully stir and dissolve;

[0077] Step 5, after dissolving, add dropwise 664kg of S-allyl thiochloroformate, the temperature of the reactor is controlled at 0-15°C, with the dropwise addition of S-allyl thiochloroformate, When the pH value of the solution in the reactor drops gradually from 11.0-12.25 to 10.0-10.9, 166 kg of 30% sodium hydroxide is added dropwise again, at this time, a double dropwise addition of S-allyl thi...

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Abstract

The invention provides a preparation method of 1-[(2-allylthio) formyl]-4-(2-methylphenyl)-5-amino-1H-pyrazole-3-ketone, and provides an alternative process for preparing the 1-[(2-allylthio) formyl]-4-(2-methylphenyl)-5-amino-1H-pyrazole-3-ketone compared with the prior art. The preparation method is simple in process and suitable for industrialization, and actual measurement results show that the yield of the 1-[(2-allylthio) formyl]-4-(2-methylphenyl)-5-amino-1H-pyrazole-3-ketone (in terms of 5-amino-4-(2-methylphenyl)-1, 2-dihydro-3H-pyrazole-3-ketone) reaches 90% or above, and the yield is higher.

Description

technical field [0001] The present invention relates to the technical field of compound preparation, in particular to a 1-[(2-propenylthio)formyl]-4-(2-methylphenyl)-5-amino-1H-pyrazole-3- Method for the preparation of ketones. Background technique [0002] 1-[(2-propenylthio)formyl]-4-(2-methylphenyl)-5-amino-1H-pyrazol-3-one is a pyridine-based compound developed by Sumitomo Chemical Co., Ltd. Active ingredient of the heterocyclic fungicide fungicide Prolectus. Pathogen mechanism of action of 1-[(2-propenylthio)formyl]-4-(2-methylphenyl)-5-amino-1H-pyrazol-3-one via inhibition of ergosterol biosynthetic pathway , showing inhibition of mycelial growth and spore germination and pollen tube growth. [0003] In the prior art, the preparation method of 1-[(2-propenylthio)formyl]-4-(2-methylphenyl)-5-amino-1H-pyrazol-3-one has complicated process , the problem of low product yield, therefore, the research and development of new 1-[(2-propenylthio)formyl]-4-(2-methylphenyl)-5...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/52
CPCC07D231/52
Inventor 孙鹏朱虎郝建马文涛袁震
Owner 山东广浦生物科技有限公司