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Catalytic synthesis process of key intermediate of emamectin

A technology of methylamino abamectin and synthesis process, applied in the directions of organic chemistry, organic chemical methods, sugar derivatives, etc., can solve the problems of low yield, high pollution, poor selectivity, etc., achieve high yield, reduce production Cost, fast response effect

Active Publication Date: 2019-01-04
HEBEI VEYONG BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problems of high pollution, low yield and poor selectivity in the prior art, the present invention provides a catalytic synthesis process of the key intermediate of emamectin, which can selectively decompose the 5-hydroxy group under mild conditions. Esterification reaction, high yield, good selectivity

Method used

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  • Catalytic synthesis process of key intermediate of emamectin
  • Catalytic synthesis process of key intermediate of emamectin

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Get 10g of Abamectin B1 (B1a content > 90%) and dissolve it in 40g of methylene chloride at room temperature, add 1.8g of allyl chloroformate and stir for 15min, slowly add 2.8g of triethylamine, 0.5g of triethylene The mixed solution of diamine and 2.0g dichloromethane was added in about 10 minutes. After the dropwise addition was completed, it was stirred at room temperature for 10 minutes. After the reaction was completed, the next oxidation reaction was continued. Add 2.4g DMSO, 2.3g triethylamine, and slowly drop Add 2.3g of phenyl phosphate dichloride, add dropwise in 5 minutes, and stir the reaction at room temperature for 30 minutes. After the reaction was completed, 20 g of water was added, 1 mol / L hydrochloric acid was added to adjust the pH to 2.5 and stirred, the phases were separated, and the organic phase was concentrated to obtain 10.36 g of a light yellow solid with a yield of 95%.

[0027] Add 30% NaOH solution to the aqueous layer to adjust the pH valu...

Embodiment 2

[0029] Take Abamectin B2 (B2a content>90%) 10g, be dissolved in 40g methylene chloride, after dissolving completely, add 2.4g allyl chloroformate and stir at room temperature for 15min, then slowly dropwise add 3.8g tributylamine, 0.002g The mixed solution of triethylenediamine was added dropwise for 5 minutes. After the addition was completed, it was stirred at -25°C for 60 minutes to complete the reaction. Continue to the next oxidation reaction, add 2.5g DMSO, 4.0g tributylamine, and slowly drop 2.4g phenyl phosphate The diacyl chloride was added dropwise in 5 minutes, and the reaction was stirred at room temperature for 30 minutes. After the reaction, 20 g of water was added, 1 mol / L hydrochloric acid was added to adjust the pH to 3.0, stirred, phases were separated, and the organic phase was concentrated to obtain 10.54 g of a light yellow solid with a yield of 97%.

[0030] Add 30% NaOH solution to the aqueous layer to adjust the pH value to >11, let stand, and separate ...

Embodiment 3

[0032] Take Abamectin B1 (B1a content > 90%) 10g, dissolve in 40g sec-butyl acetate, add 1.9g allyl chloroformate after dissolving completely, stir at room temperature for 15min, then slowly add 1.5g ethyldiisopropylamine dropwise , a mixed solution of 1.2g triethylamine and 0.4g tetramethylethylenediamine, the dropwise addition is completed in 5 minutes, after the addition is completed, stir at 0°C for 40 minutes to complete the reaction, continue the next oxidation reaction, add 2.4g DMSO, 3.0g Ethyldiisopropylamine, 1.8g of solid phosgene in 3ml of dichloromethane solution was slowly added dropwise, the dropwise addition was completed in 5 minutes, and the reaction was stirred at room temperature for 30 minutes. After the reaction, add 20 g of water, add 1 mol / L hydrochloric acid to adjust the pH to 3.0, stir, and separate phases. The organic phase was concentrated to obtain 10.15 g of a light yellow solid with a yield of 93%.

[0033] Add 30% NaOH solution to the aqueous ...

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Abstract

The invention relates to the technical field of synthesis of pesticide intermediates and particularly discloses a catalytic synthesis process of a key intermediate of emamectin. According to the process, a specific catalyst, namely triethylenediamine or tetramethylethylenediamine, for an esterification reaction is selected, and a method for performing the esterification reaction on a 5-hydroxyl group under mild conditions is determined. The method has high selectivity to the 5-hydroxyl group, a good reaction effect and a high yield, an oxidation reaction of a 4-hydroxyl group in the next stepcan be carried out without treatment after the esterification reaction is completed, an acid binding agent can be recovered after the reaction is completed, the environmental pollution is reduced, andthe production cost is reduced.

Description

technical field [0001] The invention relates to the technical field of synthesis of pesticide intermediates, in particular to a catalytic synthesis process of a key intermediate of emamectin. Background technique [0002] As a mature insecticide, emamectin benzoate has a large annual output and is widely used. Patent US5362863 and US005288710 have reported the synthetic method of emamectin, and it is to take abamectin as raw material, carries out esterification reaction and oxidation reaction at 5 and 4 " position hydroxyl respectively and makes intermediate, then by The intermediate is further prepared to emamectin benzoate. And the 5-position and 4”-position hydroxyl of abamectin has higher activity, so the selectivity of the reaction needs to be improved. The traditional production method uses tetramethylethylenediamine as an acid-binding agent at low temperature (-30~-20°C), selectively esterifies the 5-position hydroxyl group, and then oxidizes the 4”-position hydroxyl...

Claims

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Application Information

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IPC IPC(8): C07H17/08
CPCC07B2200/07C07H17/08
Inventor 王博田学芳贾成国
Owner HEBEI VEYONG BIO CHEM
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