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Process for producing insecticide intermediate

A technology of molecular formula and compound, applied in the field of preparation of pesticide intermediates, can solve problems such as oxidation of hydrazine derivatives that have not yet been understood and have not been made

Inactive Publication Date: 2005-01-12
拜耳有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the applicant of the present invention is not aware of any other information on the oxidation of hydrazine to form hydrazones
Furthermore, the description by Kim and Choi is limited to derivatives of unsubstituted phenylhydrazines and does not make any suggestion that the oxidation of hydrazine derivatives of fumaronitrile can be achieved

Method used

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  • Process for producing insecticide intermediate
  • Process for producing insecticide intermediate
  • Process for producing insecticide intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (Scheme Sc1)

[0049] Ammonia (20 μl 8% ammonia in water) was added to 2-(2,6-dichloro-4-trifluoromethylphenylhydrazono)succinonitrile (0.077 g) and ethanol (1 ml) at 0°C In a mixture with water (0.2 mL), after 10 min the mixture was extracted (dichloromethane) and evaporated to give the title compound (0.076 g, 97% yield) in 98% purity (from Hplc).

Embodiment 2

[0051] Preparation of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (Scheme Sc1)

[0052] 2-(2,6-dichloro-4-trifluoromethylphenylhydrazono)succinonitrile (1.0 g) and sodium bicarbonate (40 ml saturated aqueous solution) and dichloromethane (915 ml) at 20°C , and the pH value was 9 and stirred for 3 hours. Sodium carbonate solution was added until the pH was 11 and stirring was continued overnight. A small amount of sodium hydroxide solution was added to make the pH value reach 12, and then a small amount of Aliquat336 (trademark, trioctanoylmethylammonium chloride) was added after 3 hours, and the reaction was completed after 2 hours. The dichloromethane extracts were washed (water and brine), dried (sodium sulfate) and evaporated to give the title compound.

Embodiment 3

[0054] Preparation of 2-(2,6-dichloro-4-trifluoromethylphenylhydrazono)succinonitrile (Scheme Sc2)

[0055] A mixture of 2-(2,6-dichloro-4-trifluoromethylphenylhydrazino)succinonitrile (0.323 g) and copper dichloride (0.175 g) was heated at 60°C in chlorobenzene for 6 hours, filtered and evaporated to give a 7:1 mixture of the title compound and 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole on silica gel Column chromatography eluting with dichloromethane gave the pure title compound as a mixture of cis and trans isomers, NMR (trans isomer) 3.6 (s, 2H), 7.57 (s, 2H), 8.82(s, 1H, available D 2 O exchange), NMR (cis isomer) 3.56 (s, 2H), 7.59 (s, 2H), 8.27 (s, 1H, available D 2 O exchange).

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Abstract

The invention relates to a process for the preparation of compounds having formula (I) wherein W, R2, R3, R5 and R6 are as defined in the description, which are useful as intermediates in the synthesis of pesticidally active compounds.

Description

[0001] This application is a divisional application of Chinese patent application No. 98802977.4 filed on February 25, 1998, entitled "Preparation Method of Pesticide Intermediate". technical field [0002] The invention relates to a preparation method of an insecticide intermediate, a novel 2-arylhydrazinosuccinonitrile compound, and a 2-arylhydrazinosuccinonitrile compound. technical background [0003] Published European Patent Nos. 0295117 and 0234119 describe the preparation of insecticidally active phenylpyrazole compounds and 5-amino-1-aryl-3-cyanopyrazole intermediate compounds useful in the synthesis. Various methods for the preparation of these compounds are known. However, there is a need to provide improved methods for the preparation of these compounds and their intermediate compounds. [0004] Arylhydrazines are known to undergo Michael addition reactions with electron-deficient alkenes such as acrylonitrile in polar protic solvents such as alcohols, followed ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B61/00C07C253/30C07C255/66C07D213/77C07D231/38C07D401/04
CPCC07D231/38C07C255/66C07D401/04C07D231/14C07D213/76C07D213/61C07D213/26C07D213/30C07D213/71C07C251/76C07C243/22
Inventor T·达席尔瓦J·-E·安塞尔
Owner 拜耳有限责任公司