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Green synthetic method for methyl-3-ethyl-4-chlorin-5-pyrazol formyl chloride

A technique for pyrazole carboxyl chloride and its synthesis method, which is applied in the field of chemical synthesis of 1-methyl-3-ethyl-4-chloro-5-pyrazole carboxyl chloride, and can solve potential safety hazards in the use process and difficulties in storage and transportation , safety hazards and other issues, to achieve the effect of no three wastes, low production cost, simple and safe operation

Inactive Publication Date: 2008-11-19
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because phosgene is a highly toxic gas that is strictly controlled and restricted internationally, there are great safety hazards in both laboratory work and industrial production; the use of thionyl chloride leads to the emission of sulfur dioxide in waste gas; trichlorochloroformate Methyl ester (diphosgene) decomposes into phosgene when encountering activated carbon, iron or organic amine, and it is difficult to store and transport. Therefore, there is a big safety hazard in the process of use

Method used

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  • Green synthetic method for methyl-3-ethyl-4-chlorin-5-pyrazol formyl chloride
  • Green synthetic method for methyl-3-ethyl-4-chlorin-5-pyrazol formyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add 19mmol of 1-methyl-3-ethyl-4-nitro-5-pyrazolecarboxylic acid, 0.019mmol of pyridine and 20mL of benzene into a 100mL three-necked flask, and dropwise add 10mL of 5.7mmol bis(tris Chloromethyl ester) benzene solution of carbonate, dropwise, keep warm for 20h, after the reaction is over, concentrate under reduced pressure to recover the solvent, and finally collect the fraction at 120~123°C / 1333Pa to obtain a purity of 97% and a yield of 93%. 1-Methyl-3-ethyl-4-chloro-5-pyrazolecarbonyl chloride Light yellow transparent liquid. Boiling point: 297°C / 760mmHg.

Embodiment 2

[0017] Add 19mmol of 1-methyl-3-ethyl-4-nitro-5-pyrazolecarboxylic acid, 1.9mmol of triethylamine and 30mL of toluene into a 100mL three-necked flask, and dropwise add 10mL containing 15.2mmol of bis The toluene solution of (trichloromethyl)carbonate, dropwise, heat preservation reaction for 8h, the reaction is completed, the solvent is concentrated and recovered under reduced pressure, and finally the fraction at 120~123°C / 1333Pa is collected to obtain a purity of 98% and a yield of 92 % of 1-methyl-3-ethyl-4-chloro-5-pyrazolecarbonyl chloride light yellow transparent liquid.

Embodiment 3

[0019] Add 19mmol of 1-methyl-3-ethyl-4-nitro-5-pyrazolecarboxylic acid, 0.76mmol of N-methylpyrrole and 40mL of dichloromethane into a 100mL three-necked flask, and drop 10mL of Containing 9.5mmol of bis(trichloromethyl)carbonate in toluene solution, after dripping, heat preservation reaction for 16h, after the reaction was completed, concentrated under reduced pressure to recover the solvent, and finally collected the fraction at 120~123°C / 1333Pa to obtain a purity of 97%. The yield was 94% of 1-methyl-3-ethyl-4-chloro-5-pyrazolecarbonyl chloride as light yellow transparent liquid.

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Abstract

The invention discloses an environmental-friendly method for synthesizing 1-methyl-3-ethide-4-chlorine-5-pyrazole formyl chloride. The synthesizing method takes 1- methyl-3-ethide-4-chlorine-5- pyrazole formic acid which is shown as a formula (II) and bis (trichloromethyl) carbonate which is shown as a formula (III) as raw materials and takes organic amine as a catalyst. The raw materials and the catalyst react sufficiently in an organic solvent at a temperature of between 20 and 80 DEG C; and the 1-methyl-3-ethide-4-chlorine-5-pyrazole formyl chloride which is shown as the formula (I) is obtained by processing the reaction fluid. Compared with prior art, the method has advanced process flow, reasonable process conditions, and cheap and available raw materials, avoids the phosgene, the Cloruro de tionilo and the trichloromethyl chloroformate, and has simple and safe operation, high reaction yield coefficient, low production cost, great implementation value and social and economical benefits and basically does not have 'three wastes'.

Description

(1) Technical field [0001] The present invention relates to a chemical synthesis method of 1-methyl-3-ethyl-4-chloro-5-pyrazole carboxylic acid chloride, 1-methyl-3-ethyl-4-chloro-5-pyrazole carboxylic acid chloride It is an important intermediate for the synthesis of new acaricide tebufenpyrad. (2) Background technology [0002] Before the present invention was made, the existing method for chemically synthesizing 1-methyl-3-ethyl-4-chloro-5-pyrazolecarbonyl chloride was from 1-methyl-3-ethyl-4-chloro-5- Synthesized from pyrazole carboxylic acid and phosgene, thionyl chloride or trichloromethyl chloroformate as raw materials, such as JP03206079, JP0469379, JP03153668, etc. Because phosgene is a highly toxic gas that is strictly controlled and restricted internationally, there are great safety hazards in both laboratory work and industrial production; the use of thionyl chloride leads to the emission of sulfur dioxide in waste gas; trichlorochloroformate Methyl ester (diph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/16
Inventor 谭成侠翁建全曹耀艳
Owner ZHEJIANG UNIV OF TECH
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