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Synthesis method of 4-chloro-2-cyano-1-dimethylamino-sulfonyl-5-(4-methylphenyl)imidazo

A technology of dimethylaminosulfonyl and oximemethyne imidazole, which is applied in the field of synthesis of 4-chloro-2-cyano-1-dimethylaminosulfonyl-5-imidazole, can solve solvent waste, Long response time, increased waste water discharge and other problems, to achieve the effect of saving costs, reducing waste water discharge, and reducing environmental pressure

Active Publication Date: 2012-04-25
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But adopt this method 4-chloro-2-cyano group-1-dimethylaminosulfonyl-5-(4-methylphenyl) imidazole total yield still can only reach 42.5%, and the reaction time is longer, reaches 18~33 hours, adopt N in addition reaction, N-dimethylformamide is made solvent, and after reaction finishes, reaction solution is directly discharged into water, and solvent can't be recovered, and not only causes the waste of solvent, and makes waste water discharge increase, causes huge environmental pollution

Method used

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  • Synthesis method of 4-chloro-2-cyano-1-dimethylamino-sulfonyl-5-(4-methylphenyl)imidazo

Examples

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Embodiment 1

[0017] a. Synthesis of 2,2-Dichloro-4′-methylacetophenone

[0018] In a 1000ml four-necked flask equipped with a thermometer, agitator and reflux condenser, add 450ml of toluene, 80.1g of anhydrous aluminum trichloride, add 88.5g of dichloroacetyl chloride dropwise, and control the temperature at 25±5°C. After the addition, the temperature was raised to 80°C and reacted for 2 hours. The reaction solution was poured into 500g of crushed ice, stirred until the ice was completely dissolved, separated, the organic phase was evaporated to remove the toluene, and recrystallized with 50ml of absolute ethanol to obtain 115.7g of white solid.

[0019] b. Synthesis of 1-hydroxy-4(5)-(4-methylphenyl)-2-oximinomethine imidazole-3-oxo

[0020] Add 64.1g of 2,2-dichloro-4'-methylacetophenone, 104.3g of hydroxylamine hydrochloride, 200ml of methanol, and 100ml of water into a 1000ml four-necked flask equipped with thermometer, stirrer and reflux condenser, and heat to reflux , React for 2 hours, ...

Embodiment 2

[0027] a. Synthesis of 2,2-Dichloro-4′-methylacetophenone

[0028] In a 1000ml four-necked flask equipped with a thermometer, agitator and reflux condenser, add 450ml of toluene, 80.1g of anhydrous aluminum trichloride, add 88.5g of dichloroacetyl chloride dropwise, and control the temperature at 25±5°C. After the addition, the temperature was raised to 80°C and reacted for 2 hours. The reaction solution was poured into 500g of crushed ice, stirred until the ice was completely dissolved, separated, the organic phase was evaporated to remove toluene, and recrystallized with 50ml of absolute ethanol to obtain 115.7g of white solid.

[0029] b. Synthesis of 1-hydroxy-4(5)-(4-methylphenyl)-2-oximinomethine imidazole-3-oxo

[0030] Add 64.1g of 2,2-dichloro-4'-methylacetophenone, 104.3g of hydroxylamine hydrochloride, 200ml of methanol, and 100ml of water into a 1000ml four-necked flask equipped with thermometer, stirrer and reflux condenser, and heat to reflux , React for 2 hours, add ...

Embodiment 3

[0035] The method is basically the same as that of Example 1, except that in step b, "hydroxylamine hydrochloride" is replaced with hydroxylamine sulfate. The total yield of cyanoxaazole is 59.5% and the content is 98.4%.

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Abstract

The invention discloses a synthesis method of 4-chloro-2-cyano-1-dimethylamino-sulfonyl-5-(4-methylphenyl)imidazo, which aims to solve the technical problems of long reaction time, low yield and environment pollution of the prior art. The method is used for preparing 2,2-dichloro-4'-methyl acetophenone as an intermediate through an acylation reaction of methylbenzene and dchloroethanoyl chloride and preparing 4(5)-chloro-2-cyano-5(4)-(4-methylphenyl)imidazo as an intermediate by taking ethyl acetate and the like as solvent, N-succinchlorimide as chlorinating agent and sodium dithionite and the like as reductant. The synthesis method has short reaction time, high yield and total yield up to 61.7% and is mainly used for preparing the 4-chloro-2-cyano-1-dimethylamino-sulfonyl-5-(4-methylphenyl)imidazo.

Description

Technical field [0001] The invention relates to a method for synthesizing 4-chloro-2-cyano-1-dimethylaminosulfonyl-5-(4-methylphenyl)imidazole. Background technique [0002] 4-Chloro-2-cyano-1-dimethylaminosulfonyl-5-(4-methylphenyl)imidazole (i.e. Cyanofamidazole) is a new type of imidazole sterilization developed by Japan Ishihara Industry Co., Ltd. Agent. It is an inhibitor of mitochondrial respiration, acting on the Q of the mitochondrial complex i Position, different from the Q of methacrylate fungicides acting on mitochondrial complex 0 It is the only agricultural fungicide that has been developed to act on Q i The fungicide at the site has a new mechanism of action, and it is not easy to produce cross-resistance with other types of fungicides. Its characteristics are also that it is a high-activity, low-toxicity fungicide, and has a strong preventive effect. It has a long lasting period after application, is resistant to rain erosion, has high safety to humans, animals an...

Claims

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Application Information

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IPC IPC(8): C07D233/90
Inventor 李宗英宁斌科王月梅王列平许诚苏天铎刘康云钱一石徐泽刚薛超李勇智孙侨南齐岩张媛媛刘军黄晓瑛卫天祺
Owner XIAN MODERN CHEM RES INST
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