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A synthesis method and a technology for intermediates, which are applied in the field of chemistry, can solve the problems of low production yield of fipronil intermediates, difficult to industrialized production, complicated operations, etc., and achieve the effects of low production cost, simple method and simple operation.
Inactive Publication Date: 2012-09-26
HENAN UNIV OF CHINESE MEDICINE
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[0005] In view of the above situation, in order to overcome the defects of the prior art, the purpose of the present invention is to provide a synthetic method of fipronil intermediate, w...
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Embodiment 1
[0016] Add 0.3mol (ie 98.3g) of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole to 300ml of acetone, heat to 0.4 atm. 30 ~ 35 ℃, evaporate 50mL of acetone, then cool to 20 ℃, quickly add 0.24 moles of sulfur monochloride (ie 33.3g), and then react at 35 ℃ and under the negative pressure of -0.03--0.01MPa for 0.5 hours to obtain The mixture was allowed to stand at 35°C and 1 atmosphere for 0.5h, hydrogen chloride was removed, triethylamine was added dropwise to adjust pH=7, cooled to 5°C, filtered to obtain filtrate, the filtrate was washed with water, and dried to obtain 5-amino -1-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyanopyrazol-4-ylbissulfide 104.3g, content 97.0%, yield 95.8%, 1H NMR (300MHz, DMSO-d6): δ 7.98 (s, 4H, Ph), 6.69 (s, 4H, NH 2 ).
Embodiment 2
[0018] Add 0.3mol (ie 98.3g) of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole to 300ml of ethanol, heat to 0.6 atmospheres 65 ~ 70 ℃, evaporate 50mL of ethanol, then cool to 20 ℃, quickly add 0.18 moles of sulfur monochloride (ie 25g), and then react at 40 ℃ and under the negative pressure of -0.06--0.04MPa for 0.5 hours to obtain a mixture , the mixture was allowed to stand at 40°C and 1 atmosphere for 0.5h, hydrogen chloride was removed, and the PH=7 was adjusted with monomethylamine, cooled to 5°C, and the filtrate was filtered, washed with water, and dried to obtain 5-amino- 1-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyanopyrazol-4-ylbissulfide 101.4 g, content 96.8%, yield 93.0%.
Embodiment 3
[0020] Add 0.3mol (ie 98.3g) of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole to 300ml of acetonitrile, heat to 0.3 atm. 65~70 ℃, evaporate 50mL of acetonitrile, then cool to 20 ℃, quickly add 0.15 moles of sulfur monochloride (ie 20.8g), and then react for 0.5 hours at 40 ℃, under the negative pressure of -0.08--0.07MPa to obtain The mixture was allowed to stand at 45°C and 1 atmosphere for 0.5h, the hydrogen chloride was removed, the pH was adjusted to 7 with ammonia, cooled to 5°C, the filtrate was filtered, the filtrate was washed with water, and dried to obtain 5-amino-1 -(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyanopyrazol-4-ylbissulfide 103.3 g, content 97.2%, yield 95.1%.
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Abstract
The invention relates to a synthesizing method for fipronil intermediates. The synthesizing method for the fipronil intermediates effectively solves problems of low production yield in preparation of the fipronil intermediates, complicated operation, low purity and difficulty in industrialized production. The method includes steps of adding 5-amino-3-cyano-1-(2, 6-dichloro-4-trifluoromethyl phenyl) pyrazole into a polar solvent at first and blending the 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl phenyl) pyrazole evenly, heating the 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl phenyl) pyrazole to 30-70 DEG C under 0.3-0.6 atmosphere, distilling one sixth of the polar solvent, and then cooling the 5-amino-3-cyano-1-(2, 6-dichloro-4-trifluoromethyl phenyl) pyrazole to 20 DEG C, quickly adding sulfur monochloride to react for half an hour under the conditions of 35-40 DEG C and negative pressure of -0.095--0.01MPa, obtaining a mixture which is standing for half an hour under the conditions of 35-50 DEG C and one atmosphere so as to remove hydrogen chloride, adding an amine regulator to regulate a PH value as 7, cooling the mixture to </=5 DEG C, filtering to obtain a filtered object which is washed by water, and drying to obtain 5-amino-1-(2,6-dichloro-4-trifluoromethyl phenyl)-3-cyano pyrazole-4-base double sulfur. The synthesizing method for the fipronil intermediates is prepared by simple process and operated under mild reaction conditions, high in production yield and purity, low in production cost, easy to produce in an industrialized manner and capable of serving as the intermediate to effectively prepare fipronil.
Description
technical field [0001] The invention relates to the field of chemistry, in particular to a method for synthesizing a fipronil intermediate. Background technique [0002] Fipronil is a phenylpyrazole insecticide with a wide insecticidal spectrum. It mainly has gastric toxicity to pests, and also has contact killing and certain systemic effects. Its mechanism of action is to hinder insect γ-aminobutyric acid Controlled chloride metabolism, so it has high insecticidal activity against important pests such as aphids, leafhoppers, planthoppers, Lepidoptera larvae, flies and Coleoptera, and has no phytotoxicity to crops. The agent can be applied to the soil or sprayed on the leaves. Applying to the soil can effectively control corn root leaf beetle, wireworm and cutworm. When sprayed on the leaves, it has a high level of control effect on diamondback moth, cabbage butterfly, rice thrips, etc., and has a long lasting effect. Although my country has stipulated that starting from ...
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