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Preparation technology of chlorantraniliprole impurity

A technology for the preparation of chlorantraniliprole and its preparation process, which is applied in the field of the preparation process of chlorantraniliprole impurities, and can solve problems such as consumer hazards, drug properties/toxicological effects, and environmental pollution

Active Publication Date: 2018-05-15
LIER CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because it is not possible to control all impurities by optimizing the process, some impurities may vary greatly from batch to batch
The impurities in chlorantraniliprole may have a great impact on its medicinal properties / toxicity, etc., and residues in food may cause harm to consumers or cause environmental pollution

Method used

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  • Preparation technology of chlorantraniliprole impurity
  • Preparation technology of chlorantraniliprole impurity
  • Preparation technology of chlorantraniliprole impurity

Examples

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preparation example Construction

[0115] In the preparation process of the chlorantraniliprole impurity S2, acid-catalyzed or base-catalyzed hydrolysis can be used. Base catalysis is preferred, and optional bases include alkali metal hydroxides, such as NaOH and KOH. The reaction can be carried out in a mixed system of water and alcohol.

[0116] A more specific implementation is:

[0117] Step c, mix water, methanol and sodium hydroxide evenly, and lower the temperature to 15-25°C, add the chlorantraniliprole impurity S1 obtained in step b to it, remove methanol after the reaction is completed, add water, and use acetic acid for the water phase Extract with ethyl ester, then adjust the pH of the aqueous phase to 2-3, stir, filter, and dry to obtain the impurity S2 of chlorantraniliprole.

[0118] Wherein, in the above-mentioned process for preparing the chlorantraniliprole impurity, in step c, the molar ratio of the amount of sodium hydroxide to the added amount of the chlorantraniliprole impurity S1 is 1-3...

Embodiment 1

[0141] Example 1: Preparation of Chlorantraniliprole Impurity S1

[0142] (1) Step-by-step preparation

[0143] a. Add 10.0g M1 (0.037mol), 60.0g acetonitrile and 5.3g phosphorus oxybromide (0.018mol) into a 100mL three-necked flask, heat up to 82°C, there is obvious reflux, keep stirring for 2 hours, and naturally cool down to 50°C As follows, a dark green liquid containing flocs was obtained; 2.0 g of diatomaceous earth was added, stirred for 10 min, filtered, the filter cake was washed twice with 2.0 g of acetonitrile, and the organic phase was combined to obtain a reaction solution A; the reaction solution A was added to the saturated Sodium bicarbonate aqueous solution was extracted with dichloromethane, and the organic phase was concentrated under reduced pressure to obtain 10.3 g of M2 with a yield of 97.3% and an HPLC purity greater than 99%.

[0144] b. Take 10.3g (0.036mol) of M2 obtained in step a, 60.0g acetonitrile, 5.3g phosphorus oxybromide (0.018mol), and 15.0...

Embodiment 2

[0149] Embodiment 2: Preparation of chlorantraniliprole impurity S2

[0150] Add 10.0g of water, 15.0g of methanol and 0.6g of sodium hydroxide (0.015mol) into a 100mL single-necked bottle, stir, and when the temperature drops to room temperature, add 5.0g of chlorantraniliprole impurity S1 (0.012mol), and react for 3h , remove most of the methanol under reduced pressure, add 5.0g of water, extract twice with 5g of ethyl acetate, slowly add 2.7g of 30% hydrochloric acid solution dropwise to the water phase, adjust to pH=2~3, stir for 1h, filter, vacuum at 55°C After oven drying for 2 hours, 4.2 g of white solid chlorantraniliprole impurity S3 was obtained, with a yield of 90.2%, HPLC: 96.5%.

[0151] The hydrogen spectrum of the obtained chlorantraniliprole impurity S2 of the present embodiment is: 1 H NMR (400MHz, DMSO-d 6 ): δ8.60(d, J=2.1Hz, 1H), 8.48(d, J=2.1Hz, 1H), 6.51(s, 1H), 13.95(br, 1H).

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Abstract

The invention discloses a preparation technology of chlorantraniliprole impurity, and belongs to the technical field of organic synthesis. The technical problem to be solved by the invention is to provide a high-efficiency and low-cost technology for preparing a series of chlorantraniliprole impurity. The technology comprises the following steps: firstly using M1 as a raw material to prepare a compound M2, then carrying out oxidation and bromination with a one-pot method to prepare and obtain S1, then carrying out hydrolysis on S1 to prepare and obtain S2, and carrying out amidation on S2 to prepare S3. According to the method, separation and purification of an intermediate M2 are eliminated, the using amounts of a brominating agent and a solvent are reduced, the technological steps are shortened, the production cost is reduced, and dangerous chemical reagents such as bromine and hydrogen peroxide do not need to be used; according to the method, a series of chlorantraniliprole impuritycan be prepared, and effective guarantee is provided for production quality control for chlorantraniliprole.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a preparation process of chlorantraniliprole as an impurity. Background technique [0002] Chlorantraniliprole is a green chemical insecticide. The compound has the advantages of less dosage, high control, long-lasting effect, and no impact on humans, animals and the environment in the control of lepidopteran pests such as grain, cotton, fruit, and vegetables. Small and other characteristics, its structural formula is as follows: [0003] [0004] In the production process of chlorantraniliprole, various impurities are inevitably produced, which may come from side reactions during the synthesis of the active ingredient or from raw materials, or may be produced during the production / storage of the preparation. Because it is not possible to control all impurities by optimizing the process, some impurities may vary greatly from batch to batch. The impurities in chlorantr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 何波姚中伟李栋宏左翔程柯
Owner LIER CHEM CO LTD
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