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A kind of preparation method of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

A technology of trifluoromethylphenyl and trifluoromethylaniline, applied in the field of preparation of 5-amino-3-cyano-1-pyrazole, which can solve the problem of low product quality and high salt content in waste acid Easy to handle and other problems, achieve the effect of simple treatment, convenient recycling, and mild reaction conditions

Active Publication Date: 2020-11-17
台州达辰药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the invention is to solve the waste acid amount and / or salt content in the existing 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl) pyrazole preparation process The shortcomings of being difficult to handle and low product quality; the invention provides a preparation method of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole , using nitrosyl sulfuric acid as a diazotization reagent, diazotization of 2,6-dichloro-4-trifluoromethylaniline in an organic system, and then reacting with ethyl 2,3-dicyanopropionate High-purity 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole prepared by coupling and cyclization

Method used

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  • A kind of preparation method of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole
  • A kind of preparation method of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole
  • A kind of preparation method of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Add 150 g of sulfuric acid solution of 40% mass concentration of nitrosylsulfuric acid to a 1L four-necked bottle, start stirring, and then add 2,6-dichloro-4-trifluoromethyl to the constant pressure dropping funnel A mixed solution of 60g of aniline and 180g of dichloroethane is added dropwise at a temperature of 10-30°C, and the drop is completed in 1-2 hours. After the drop is completed, it is kept at 10-30°C for 2 hours; the diazo solution is added dropwise to 400g of ice-water bath, Control the temperature ≤ 15°C, keep it warm for 0.5 hours after dripping, let it stand for stratification, separate the water layer, add 50g of ethyl 2,3-dicyanopropionate dropwise, control the temperature at 0-30°C, and drop it at 0-30°C after dripping Stir at 30°C for 5 hours; add 300g of toluene to extract, separate layers, extract the water layer with 100g*2 toluene, combine the toluene layer, add 200g of ammonia water with a concentration of 18% dropwise, and add dropwis...

Embodiment 2

[0032] Example 2: Add 180 g of sulfuric acid solution of nitrosylsulfuric acid with a mass concentration of 30% to a 1L four-necked bottle, start stirring, and then add 2,6-dichloro-4-trifluoromethyl to the constant pressure dropping funnel A mixed solution of 60g of aniline and 240g of n-hexane, add dropwise at a temperature of 10-30°C, drop in 1-2 hours, and keep warm at 10-30°C for 3 hours after dropping; add the diazo solution dropwise into a 500g ice-water bath, and control the temperature ≤15°C, keep warm for 0.5 hours after dripping, let stand to separate the layers, separate the water layer, add 46g of ethyl 2,3-dicyanopropionate dropwise, control the temperature at 0-30°C, add drops at 0-30°C after dripping Insulate and stir for 6 hours; add 350g toluene to extract, separate layers, extract the water layer with 100g*2 toluene, combine the toluene layer, add 250g of ammonia water with a mass concentration of 15% dropwise, control the temperature at 0-15°C and add dropwi...

Embodiment 3

[0033] Example 3: Add 200 g of sulfuric acid solution of nitrosylsulfuric acid with a mass concentration of 25% to a 1L four-necked bottle, start stirring, and then add 2,6-dichloro-4-trifluoromethyl to the constant pressure dropping funnel A mixed solution of 60g of aniline and 300g of n-heptane, add dropwise at a temperature of 10-30°C, drop it in 1-2 hours, and keep it warm at 10-30°C for 5 hours; ≤15°C, keep warm for 0.5 hours after dripping, let stand to separate layers, separate the water layer, add 50g of ethyl 2,3-dicyanopropionate dropwise, control the temperature at 0-30°C and add dropwise, dropwise at 0-30°C Insulate and stir for 5 hours; add 350g toluene for extraction, separate layers, extract the water layer with 100g*2 toluene, combine the toluene layer, add 300g of ammonia water with a mass concentration of 12% dropwise, and add dropwise at 0-15°C with temperature control. Heat at 0-10°C for 10 hours, filter with suction, wash and dry to obtain 78.6g of finishe...

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Abstract

The invention provides a production method of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole. The production method of the 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole comprises the following steps: (1) adding nitrosyl sulfuric acid into a four-necked bottle, and adding mixed liquid of 4-amino-3,5-dichlorobenzotrifluoride and an organic solvent dropwise to produce diazonium liquid; (2) adding the diazonium liquid back into ice water, conducting stirring, standing for layering, separating out a water layer, and adding ethyl 2,3-dicyanopropionate dropwise for coupling; and (3) conducting toluene extraction and combining, adding ammonium hydroxide dropwise for cyclization, and conducting filtering, washing and drying to obtain a finished product. According to the production method of the 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole, the yield is high, the quality is good, single impurity is lower than or equal to 0.1%, the level ofdifficulty of treating three waste is effectively lowered, discharge of the three waste is reduced, and the cost is low.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and specifically relates to a preparation method of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole. Background technique [0002] 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole, referred to as pyrazole ring, is a synthetic high-efficiency insecticide "fipronil" (English name : fipronil, trade name: sharp proton, Regent, etc.) important intermediates, first developed and put into production by the French company Rhône-Planck, its molecular formula H 5 CIF 3 N 4 , MP: 132-141°C, CAS No.: 120068-79-63, soluble in methanol, ethanol, acetone, dichloroethane and ethyl acetate, etc., the product is light yellow or white crystal. [0003] The structural formula of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole is shown in the following formula (A): [0004] [0005] There are many synthetic patent reports of 5-amino-3-cyano-1-(2,6-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/38
CPCC07D231/38
Inventor 姜礼进蔡青峰缪炳林
Owner 台州达辰药业有限公司