Synthesis method of dinotefuran

A synthetic method, the technology of dinotefuran, is applied in the field of neonicotinoid insecticide synthesis, which can solve the problems of high toxicity of dimethyl sulfate, safety risks, and complicated steps, so as to ensure the ecological environment and food safety, and avoid production The effect of dangerous operation and significant economic benefits

Active Publication Date: 2017-01-25
JIANGSU KESHENG CROP TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] Route 4 has two catalytic hydrogenation reactions, high reaction pressure, nitrogen protection is required, and there are safety risks; the reaction conditions are strict and difficult to control; the steps are complicated, the reaction selectivity is not high, and the total yield is low; a large amount of waste water is generated in the reaction Difficult to handle, severely corroded equipment
[0018] Route 5 is a c...

Method used

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  • Synthesis method of dinotefuran
  • Synthesis method of dinotefuran
  • Synthesis method of dinotefuran

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] A synthetic method for dinotefuran, comprising the following steps:

[0046] 1) Aldol condensation and reduction:

[0047]

[0048] In a 250mL three-necked round-bottom flask, dissolve 10g of sodium methoxide and 15g of γ-butyrolactone in 100g of n-hexane, stir for 1h until they are completely dissolved, then control the temperature at 10°C, and feed 10g of formaldehyde gas within 2h, then Insulate and react at 30°C for 8 hours, take samples to determine the normalized content of γ-butyrolactone ≤ 0.5%, the aldol condensation reaction is completed, remove the residual formaldehyde gas in the n-hexane solution under low temperature and negative pressure, neutralize it with hydrochloric acid to weak acidity, After filtering, the solvent was distilled off from the filtrate under negative pressure to obtain 18.5 g of a-hydroxymethyl-γ-butyrolactone with a content of 98% and a yield of 90%.

[0049] Dissolve 18.5g of a-hydroxymethyl-γ-butyrolactone in 60mL of tetrahydrofur...

Embodiment 2

[0064] A synthetic method for dinotefuran, comprising the following steps:

[0065] 1) Aldol condensation and reduction:

[0066]

[0067] In a 250mL three-neck round bottom flask, dissolve 10g sodium methoxide and 15g γ-butyrolactone in 100g n-hexane, stir for 3 hours until they are completely dissolved, then control the temperature at 50°C, and feed 10g of formaldehyde gas within 4 hours, then Insulate and react at 60°C for 13 hours, take samples to determine the normalized content of γ-butyrolactone ≤ 0.5%, after the aldol condensation reaction is completed, remove the residual formaldehyde gas in the n-hexane solution under low temperature and negative pressure, neutralize it with hydrochloric acid to weak acidity, After filtering, the solvent was distilled off from the filtrate under negative pressure to obtain 18.5 g of a-hydroxymethyl-γ-butyrolactone with a content of 97% and a yield of 91%.

[0068] Dissolve 18.5g of a-hydroxymethyl-γ-butyrolactone in 60mL of tetra...

Embodiment 3

[0083] A synthetic method for dinotefuran, comprising the following steps:

[0084] 1) Aldol condensation and reduction:

[0085]

[0086] In a 250mL three-necked round-bottom flask, dissolve 10g of sodium methoxide and 15g of γ-butyrolactone in 100g of n-hexane, stir for 2 hours until they are completely dissolved, then control the temperature at 30°C, and feed 10g of formaldehyde gas within 3 hours, then Insulate and react at 40°C for 10 hours, take samples to determine the normalized content of γ-butyrolactone ≤ 0.5%, after the aldol condensation reaction is completed, remove the residual formaldehyde gas in the n-hexane solution under low temperature and negative pressure, neutralize it with hydrochloric acid to weak acidity, After filtration, the solvent was distilled off from the filtrate under negative pressure to obtain α-hydroxymethyl-γ-butyrolactone, 18.5 g, content 96%, yield 91%.

[0087] Dissolve 18.5g of a-hydroxymethyl-γ-butyrolactone in 60mL of tetrahydrofu...

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Abstract

The invention discloses a synthesis method of dinotefuran. The synthesis method includes: using gamma-butyrolactone as a raw material, and preparing 3-hydroxymethyltetrahydrofuran through two-step reaction of Aldol condensation and reduction; synthesizing 3-tetrahydrofuran methylamine through a Gabriel method; using dimethyl carbonate (DMC) as a methylation reagent to synthesize with urea to obtain O-methylisourea; performing nitration to synthesize O-methyl-N-nitroisourea; reacting with methylamine to synthesize 1, 3-dimethyl-2-nitroisourea; subjecting 3-tetrahydrofuran methylamine and 1, 3-dimethyl-2-nitroisourea to a one-step process to synthesize dinotefuran through SN2dimolecular nucleophilic substitution. Dimethyl carbonate which is nontoxic is adopted as the methylation agent, methylation reaction yield is greater than or equal to 95%, O-methylisourea content is greater than or equal to 96%, byproducts are carbon dioxide and methanol, the process is environment-friendly, and total yield of dinotefuran is greater than or equal to 50%. The synthesis method can lower production cost, has the advantages of little three wastes, simple aftertreatment and environment friendliness, is suitable for industrial production and can bring about remarkable economic benefit.

Description

technical field [0001] The invention belongs to the technical field of neonicotinoid insecticide synthesis and relates to a synthesis method of dinotefuran. Background technique [0002] Dinotefuran is a new neonicotinoid insecticide developed by Mitsui East Asia Chemical Co., Ltd., Japan. It has been introduced to the market in many countries around the world, and is used to control aphids, leafhoppers and their resistant strains in various crops such as rice. [0003] There are mainly 5 synthetic routes of dinotefuran reported in the literature at present: [0004] Route 1: Use diethyl malonate as raw material to react with ethyl chloroacetate to prepare ethane-1,1,2-tricarboxylic acid ethyl ester, and react with sodium borohydride to prepare 2-hydroxymethyl-1,4- Butanediol, and then prepare 3-tetrahydrofuran methanol under the action of p-toluenesulfonic acid, and further react to prepare 3-tetrahydrofuryl methyl methanesulfonate. 1,5-Dimethyl-2-(nitroimino)-hexahydro-1...

Claims

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Application Information

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IPC IPC(8): C07D307/14C07C273/18C07C275/70
CPCC07C273/18C07D307/14C07C275/70
Inventor 吴伟熊燕玲吴重言吴静陆静徐其文
Owner JIANGSU KESHENG CROP TECH
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