Preparation method of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyanopyrazole

A technology of dichlorotrifluorotoluene and trifluoromethylphenyl is applied in the field of preparation of 5-amino-1--3-cyanopyrazole, and can solve the problem of inconvenient on-site operation, low safety factor and large amount of solid waste and other problems, to achieve the effect of improving recycling rate, reducing equipment requirements, and reducing raw material costs

Inactive Publication Date: 2016-11-16
潍坊鑫诺化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the above method, there are some problems such as high price of raw materials, low safety factor, inconvenient on-site operation, large amount of waste water and so

Method used

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  • Preparation method of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyanopyrazole
  • Preparation method of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyanopyrazole
  • Preparation method of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyanopyrazole

Examples

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Example Embodiment

[0033] A preparation method of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyanopyrazole includes the following steps:

[0034] a) Using 3,4-dichlorobenzotrifluoride and dimethylamine as raw materials, using caustic soda as acid binding agent, and using sodium dithionite and benzyltriethylammonium chloride as catalysts to obtain 2-chloro-4- Trifluoromethyl-N,N-dimethylaniline;

[0035] b) Add sulfuryl chloride, liquid caustic soda, and azobisisobutyronitrile as a catalyst to the 2-chloro-4-trifluoromethyl-N,N-dimethylaniline obtained in step a) to obtain 2,6-di Chloro-4-trifluoromethylaniline;

[0036] c) Add 2,6-dichloro-4-trifluoromethylaniline obtained in step b) to nitrosyl sulfate for diazotization reaction, and then add ethyl 2,3-dicyanopropionate for coupling Link reaction, and then carry out cyclization reaction with concentrated ammonia water in ammonia water medium to obtain.

[0037] The raw materials used in the invention are cheap and easy to obtain, which reduce...

Example Embodiment

[0052] Example 1

[0053] Under vacuum, put 1000kg of 3,4-dichlorobenzotrifluoride into the autoclave, turn on the stirring, put in 150kg of caustic soda, 25kg of sodium dithionite, 1.8kg of benzyltriethylammonium chloride, turn off the vacuum, and quickly put in 1800L40 % Dimethylamine aqueous solution, slowly raise the temperature to 160℃, the pressure is 2.0MPa, control the reaction rate of the raw material 3,4-dichlorobenzotrifluoride, the reaction is complete; after the reaction, slowly open the high pressure when the pressure is 0.4MPa The valve from the kettle to the washing kettle transfers the materials to the washing kettle. The remaining dimethylamine gas is condensed by the condenser and enters the secondary water absorption system for absorption; the materials are stratified in the washing kettle, and the water layer is transferred to the water absorption system as The absorption water continues to absorb the dimethylamine condensed during the next batch transfer, an...

Example

[0055] Examples 2~3

[0056] With reference to the method of Example 1, the amount of dimethylamine added was changed, and other conditions were the same as in Example 1. The results are shown in Table 1.

[0057] Table 1 The influence of the amount of dimethylamine added on the amine alkylation reaction

[0058]

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Abstract

The invention discloses a preparation method of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyanopyrazole. The preparation method comprises the following steps: carrying out the reaction for 3,4-dichlorotrifluorotoluene and dimethylamine by adopting caustic soda flakes as an acid-binding agent and adopting sodium hydrosulfite and benzyl triethyl ammonium chloride as catalysts; adding chlorosulfuric acid, liquid alkali and azodiisobutyronitrile into the obtained 2-chloro-4-trifluoromethyl-N,N-dimethylaniline to perform the reaction; and adding nitrosyl sulfate into the obtained 2,6-dichloro-4-trifluoromethyl phenylamine to carry out the diazo-reaction, then adding 2,3-ethyl dicyanopropionate to carry out the coupled reaction, and carrying out ring-closure reaction with concentrated ammonia water in an ammonia water medium to obtain the 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyanopyrazole. The caustic soda flakes is used as the acid-binding agent, and the sodium hydrosulfite and benzyl triethyl ammonium chloride are used as catalysts, so that the cost of raw materials is effectively reduced; the chlorosulfuric acid is adopted as a chlorinating agent, so that the requirement for the equipment is reduced, and the safety coefficient is increased; and a single solvent methylbenzene is adopted as a crystallizing solvent, so that the later problem such as complexity in recovery and difficulty in operation can be solved.

Description

technical field [0001] The present invention relates to the field of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyanopyrazole, in particular to a 5-amino-1-(2,6- The preparation method of dichloro-4-trifluoromethylphenyl)-3-cyanopyrazole. Background technique [0002] 5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyanopyrazole, referred to as pyrazole ring, is a pesticide intermediate of fluorine-containing benzopyrazole insecticides . Because this type of insecticide has the advantages of good insecticidal effect and easy degradation, pyrazole rings have attracted extensive attention. [0003] At present, the commonly used preparation method is to first synthesize 2-chloro-4-trifluoromethyl-N,N-dimethylaniline, and then synthesize 2,6-dichloro-4-trifluoromethylaniline; finally, with concentrated sulfuric acid , sodium nitrite and 2,6-dichloro-4-trifluoromethylaniline in glacial acetic acid solvent to generate diazonium salt, then esterify with ethyl 2,3-dicy...

Claims

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Application Information

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IPC IPC(8): C07D233/90
CPCC07D233/90
Inventor 王天国高林罗维政
Owner 潍坊鑫诺化工有限公司
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