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Cis-para-substituted cyclohexylamino nitrile salt and preparation method therefor

A kind of amino nitrile and substituent technology, applied in the field of cis-para-substituted cyclohexyl amino nitrile salt and its preparation, can solve the problem of poor selectivity of toluenesulfonic acid and methanesulfonic acid, affecting the subsequent use of products, and crystallization and separation of cis- Formula isomer compounds, etc.

Active Publication Date: 2020-01-14
HEBEI LANSHENG BIOTECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the inventors of the present application have found that the three inorganic acids of hydrochloric acid, sulfuric acid and phosphoric acid used in CN103270020B are not selective, and cannot be selectively formed by the salt formation of these acids with amino-4-alkoxycyclohexanecarbonitrile The cis-isomer compound is separated by crystallization; acetic acid and the above-mentioned cyclohexanecarbonitrile compound cannot be crystallized after being salified; the selectivity of p-toluenesulfonic acid and methanesulfonic acid is poor, which is not conducive to industrial production; formic acid and the above-mentioned cyclohexanecarbonitrile compound generate The salt is easy to agglomerate, has poor stability, is easy to decompose, becomes darker in color during storage, and has a lower melting point, which seriously affects the subsequent use of the product

Method used

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  • Cis-para-substituted cyclohexylamino nitrile salt and preparation method therefor
  • Cis-para-substituted cyclohexylamino nitrile salt and preparation method therefor
  • Cis-para-substituted cyclohexylamino nitrile salt and preparation method therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1 cis-p-methoxycyclohexylaminonitrile maleate

[0049]Add 600 grams of ethyl acetate solution of cis / trans-p-methoxycyclohexylaminonitrile (cis:trans=55:45) in the three-necked flask, add 39.2 grams of maleic acid (0.34 mol times), stirred for 8-12 hours, and then cooled to 5-10°C in an ice-water bath to crystallize. The precipitated maleate was filtered and rinsed with an appropriate amount of ethyl acetate. After vacuum drying at 35-40°C, white crystals of cis-p-methoxycyclohexylaminonitrile maleate (75.7 g, cis / trans ratio=95.5:4.5) were obtained.

Embodiment 2

[0050] Embodiment 2 cis-p-methoxycyclohexylaminonitrile maleate

[0051] Add 600 grams of ethyl acetate solution of cis / trans-p-methoxycyclohexylaminonitrile (cis:trans=55:45) in the three-necked flask, add 52.2 grams of maleic acid (0.45 mol times), stirred for 8-12 hours, and then cooled to 5-10°C in an ice-water bath to crystallize. The precipitated maleate was filtered and rinsed with an appropriate amount of ethyl acetate. After vacuum drying at 35-40°C, white crystals of cis-p-methoxycyclohexylaminonitrile maleate (108.1 g, cis / trans ratio=96.1:3.9) were obtained.

Embodiment 3

[0052] Embodiment 3 cis-p-methoxycyclohexylaminonitrile glycolate

[0053] Add 600 grams of ethyl acetate solution of cis / trans-p-methoxycyclohexylaminonitrile (cis:trans=55:45) into the three-necked flask, and add 34.2 hydroxyacetic acid (0.45mol moles) at 25-30°C times), stirred for 8-12 hours, and then cooled to 5-10°C in an ice-water bath to crystallize. The precipitated glycolate was filtered and rinsed with appropriate amount of ethyl acetate. After vacuum drying at 35-40°C, white cis-p-methoxycyclohexylaminonitrile glycolate crystals (92.1 g, cis / trans ratio=94:6) were obtained.

[0054] Comparative Example 1 cis-p-methoxycyclohexylaminonitrile formate

[0055] Add 600 grams of ethyl acetate solution of cis / trans-p-methoxycyclohexylaminonitrile (cis:trans=55:45) to the three-necked flask, and drop 20.7 grams of formic acid (0.45mol Mole times), when the formic acid is added to about half of the amount, a large amount of solids will precipitate out and agglomerate, co...

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Abstract

Provided are a cis-para-substituted cyclohexylamino nitrile salt as shown in formula (I) and a preparation method therefor, a use of said salt as a preparation intermediate for a pesticide such as spirotetramat, and a method for using said salt as an intermediate to prepare a pesticide such as spirotetramat. In formula (I), a para-substituent R is a C1-10 alkyl group or alkoxy group, a C1-10 alkenyl group or alkenyloxy group, a C1-10 alkynyl group or alkynyloxy group, a C1-10 cycloalkyl group or cycloalkoxy group, or a C1-10 heterocycloalkyl group or heterocycloalkoxy group containing 1-2 atoms selected from O and N, and HX is hydroxyacetic acid or maleic acid.

Description

technical field [0001] The invention relates to a cis-para-substituted cyclohexylamino nitrile salt and a preparation method thereof, the use of the salt as an intermediate for preparing pesticides, and a method for preparing pesticides using the salt as an intermediate. Background technique [0002] Chinese patent CN103270020B discloses cis-amino-4-alkoxycyclohexanecarbonitrile salt represented by the following formula: [0003] [0004] Wherein HX is hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, p-toluenesulfonic acid or methanesulfonic acid, R 1 is an alkoxy group. [0005] However, the inventors of the present application have found that the three inorganic acids of hydrochloric acid, sulfuric acid and phosphoric acid used in CN103270020B are not selective, and cannot be selectively formed by the salt formation of these acids with amino-4-alkoxycyclohexanecarbonitrile The cis-isomer compound is separated by crystallization; acetic acid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/46C07C51/41C07C57/145C07C213/08C07C215/08
CPCC07C255/46C07C57/145C07C215/08C07C2601/14C07B2200/07C07C253/30C07C253/34
Inventor 董志鹏郭庆春林斌苑立刚郭红永张志虎许峰王石华宋海文刘海龙李龙强崔德保张松赵晓东武志超王旭皓
Owner HEBEI LANSHENG BIOTECH CO LTD
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