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5-trifluoromethyl-4-nitro-2-isoxazoline compounds and preparing process therefor

A technology of trifluoromethyl and isoxazoline, applied in the field of 5-trifluoromethyl-4-nitro-2-isoxazoline compounds

Inactive Publication Date: 2013-06-26
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, all synthesis methods are building block methods in which a compound having a trifluoromethyl group is synthesized in advance, and there is no report example of a synthesis method in which a trifluoromethyl group is directly introduced into a 2-isoxazoline compound

Method used

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  • 5-trifluoromethyl-4-nitro-2-isoxazoline compounds and preparing process therefor
  • 5-trifluoromethyl-4-nitro-2-isoxazoline compounds and preparing process therefor

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Embodiment 1

[0059] The following compounds 1a to 1v, which are 5-trifluoromethyl-4-nitro-2-isoxazoline compounds represented by the above general formula (1), were produced by the following production methods, respectively.

[0060] That is, in 1 mL of solvent, dimethylformamide, 4-nitro-2-isoxazole compound (0.20 mmol) represented by the above-mentioned general formula (2), cetyltrimethyl bromide as a phase transfer catalyst were dissolved. Ammonium chloride (21.9 mg, 0.06 mmol), and sodium acetate (24.6 mg, 0.30 mmol) as base. (Trifluoromethyl)trimethylsilane (59.1 μL, 0.04 mmol) was added to the resulting solution at room temperature. Thereafter, the 4-nitro-2-isoxazole compound and (trifluoromethyl)trimethylsilane are reacted by stirring the reaction liquid at room temperature for 3 to 9 hours.

[0061] After the reaction, 1 mL of 1M hydrochloric acid was added to the reaction liquid, and the mixture was further stirred at room temperature for 1 hour to perform an acid treatment.

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Abstract

Provided are: a process for preparing 5-trifluoromethyl-4-nitro-2-isoxazoline compounds by a direct trifluoromethylation method; and the compounds. 5-Trifluoromethyl-4-nitro-2-isoxazoline compounds represented by general formula (1) are prepared by reacting a 4-nitro-2-isoxazole compound with (trifluoromethyl)trimethylsilane, preferably in a solvent in the presence of both a phase transfer catalyst and a base, followed by acid treatment if necessary. In general formula (1), R1 and R2 are each independently alkyl, alkenyl, alkynyl or aryl, each being optionally substituted.

Description

technical field [0001] The present invention relates to a 5-trifluoromethyl-4-nitro-2-isoxazoline compound and a method for producing the same. Background technique [0002] In recent years, 5-trifluoromethyl-2-isoxazoline compounds have attracted attention as pest control agents. In addition, the 5-trifluoromethyl-2-isoxazoline compound is a compound useful also as an intermediate for the production of functional materials such as pharmaceuticals and electronic materials. In view of their usefulness, a large number of 5-trifluoromethyl-2-isoxazoline compounds have been synthesized in the past. However, all synthesis methods are building block methods in which a compound having a trifluoromethyl group is synthesized in advance, and there are no reported examples of a synthesis method in which a trifluoromethyl group is directly introduced into a 2-isoxazoline compound. That is, the conventional report examples are cyclization reactions of hydroxamic acid halides and triflu...

Claims

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Application Information

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IPC IPC(8): C07D261/04C07B61/00C07D413/06
CPCC07D261/04C07D413/06
Inventor 柴田哲男河合洋幸
Owner SUMITOMO CHEM CO LTD