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Pyridine derivatives and methods of using them for the preparation of intermediate compounds for the production of sulfonylurea herbicides

A technology of compounds and derivatives, applied in the field of pyridine derivatives and intermediate compounds used to produce sulfonylurea herbicides, which can solve the problem of difficulty in completely removing Cu by-products, reducing yields, affecting fluorination reactions, etc. question

Active Publication Date: 2016-08-24
LG CHEM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, it is difficult to completely remove the Cu by-products inevitably produced by the reaction, and the above-mentioned by-products affect the subsequent fluorination reaction and reduce its yield.

Method used

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  • Pyridine derivatives and methods of using them for the preparation of intermediate compounds for the production of sulfonylurea herbicides
  • Pyridine derivatives and methods of using them for the preparation of intermediate compounds for the production of sulfonylurea herbicides
  • Pyridine derivatives and methods of using them for the preparation of intermediate compounds for the production of sulfonylurea herbicides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0140] Embodiment 1: preparation formula 3a compound

[0141] [Formula 3a]

[0142]

Embodiment 1-1

[0143] Example 1-1: Preparation of 1-(3-chloropyridin-2-yl)-2-fluoropropan-1-one (D=chloro, Y=fluoro)

[0144] Under nitrogen atmosphere, hexane (40 mL) and N,N-dimethylaminoethanol (3.14 g, 35.2 mmol) were added to the reaction vessel and cooled to -5°C. n-Butyllithium (2.5M in hexane, 70 mmol) was added dropwise to the reaction solution, and the mixture was stirred for 1 hr and cooled to -41°C. 3-Chloropyridine in hexane (2.04 g, 18 mmol) was added dropwise to the mixture. After the addition, the reaction mixture was cooled to -78°C, and 2-fluoropropionic acid morpholinamide (5.64 g, 35 mmol) in hexane was added dropwise to the mixture. The reaction mixture was stirred for 2 hours and then heated to -20°C. Propionic acid (9.13 g, 123 mmol) was added dropwise to the mixture to terminate the reaction. The reaction solution was heated to 0°C. After adding water, the solution was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and...

Embodiment 1-2

[0146] Example 1-2: Preparation of 1-(3-fluoropyridin-2-yl)-2-fluoropropan-1-one (D=fluorine, Y=fluorine)

[0147] According to the same procedure of Example 1-1, reaction of 3-fluoropyridine (1.75 g, 18 mmol) instead of 3-chloropyridine provided the title compound (2.00 g, 65%).

[0148] 1 H NMR (CDCl 3 , δ): 8.51-8.50 (m, 1H), 7.60-7.54 (m, 2H), 6.15 (dq, J=6.7, 48.9Hz, 1H), 1.67 (dd, J=6.7, 23.8Hz, 3H)

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Abstract

The present invention relates to novel methods for the preparation of key intermediate compounds for the production of fluoroalkylpyridine-sulfonylurea derivatives exhibiting excellent herbicidal activity for the preparation of novel pyridine derivatives , and methods for their preparation.

Description

【Technical field】 [0001] The present invention relates to a novel process for the preparation of key intermediate compounds for the production of fluoroalkylpyridine-sulfonylurea derivatives exhibiting excellent herbicidal activity, new pyridine derivatives for the preparation and for the preparation of its method. 【Background technique】 [0002] The compound of the following formula 1 is called flucetosulfuron, which has excellent herbicidal activity (WO 2002 / 030921). According to JP Patent Publication No. 2003-335758, the compound of formula 1 is prepared from the intermediate compound of formula 2 below: [0003] 【Formula 1】 [0004] [0005] [Formula 2] [0006] [0007] A is for C 3 -C 5 -Alkyl or C 3 -C 6 -Cycloalkyl, or represents unsubstituted or selected from C 1 -C 2 -Alkyl and C 1 -C 2 - alkoxy substituents 1- to 5-substituted benzyl; and [0008] Y represents fluorine, chlorine or bromine. [0009] In order to introduce the key residue fluorine...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/61C07D213/62C07D401/12A01N43/54
CPCA01N47/36C07D213/61C07D213/70C07D213/71A01N43/34
Inventor 安世昌金淑姬李周泳尹胄镛尹万泳
Owner LG CHEM LTD