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Method for preparing 2-amino-3,5-dichloro-N-isopropylbenzamide

A technology of isopropyl benzamide and isopropylamine, which is applied in the field of preparing 2-amino-3, can solve the problems of large environmental pollution, extraordinary production requirements, and high cost of three wastes treatment, and achieve high total yield and simple post-treatment Effect

Active Publication Date: 2019-07-12
中翌科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method reported in the patent has a high yield, but it needs to be divided into steps. In the process of industrial scale-up, separation and drying need to be added, and the investment in manpower and equipment is large.
Sulfuryl chloride is used in the chlorination reagent, and a large amount of sulfur dioxide gas produced is relatively polluting to the environment. It needs to be absorbed by alkali, which is also very demanding on production, and the cost of three wastes is high.

Method used

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  • Method for preparing 2-amino-3,5-dichloro-N-isopropylbenzamide
  • Method for preparing 2-amino-3,5-dichloro-N-isopropylbenzamide

Examples

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Embodiment 1

[0014] At room temperature, in a 1000ml round bottom flask, add isatoic anhydride (50g, 306.5mmol), dichloroethane 300ml, and slowly add isopropylamine (20.8g, 352.4mmol) dropwise at 30-35°C. After the dropwise addition, the reaction was completed after stirring for about 2 hours, and the liquid phase detection of isatoic anhydride was less than 2%. Cool down to 20°C, add dichlorhein (66.4g, 337.2mmol) in batches, keep the temperature at 20-25°C, stir for 12h, the liquid phase detection of compound III is less than 1%, stop the reaction. When about 150ml of the reaction system was distilled off under reduced pressure, the temperature of the system was lowered to below 5°C, filtered with suction, and the solid was washed twice with 50°C water (100ml) and dried by suction. Transfer to a reaction bottle, add anhydrous methanol (200ml), heat to 60°C, cool to below 5°C, filter with suction, and dry to obtain 62g of white solid, the yield of 2 steps is 83%, the purity of liquid phas...

Embodiment 2

[0017] At room temperature, add isatoic anhydride (3kg, 18.39mol) and 18L dichloroethane into a 50L reactor, and slowly add isopropylamine (1.248kg, 21.144mol) dropwise at 30-35°C. After the dropwise addition, the reaction was completed after stirring for about 2 hours, and the liquid phase detection of isatoic anhydride was less than 2%. Cool down to 20°C, add dichlorhein (3.984kg, 20.232mol) in batches, keep the temperature at 20-25°C, stir for 13h, the liquid phase detection of compound III is less than 1%, stop the reaction. When about 10 L of the reaction system was distilled off under reduced pressure, the temperature of the system was lowered to below 5°C, filtered with suction, and the solid was washed twice with 50°C water (2L) and dried by suction. Transfer to a reaction kettle, add anhydrous methanol (10L), heat to 60°C, cool to below 5°C, filter with suction, and dry to obtain 3.68kg of white solid, the yield of 2 steps is 81%, the purity of liquid phase detection ...

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Abstract

The invention discloses a method for preparing 2-amino-3,5-dichloro-N-isopropylbenzamide. The method comprises the following steps: (1) preparation of mixed amide: adding isatoic anhydride to a reaction solvent with the reaction concentration, which is a ratio of the solvent volume to the weight of isatoic anhydride, of 5-10 times and the reaction temperature at 20-40 DEG C, adding isopropylaminedropwise, monitoring the reaction progress in the liquid phase, and performing a reaction of a next step directly without separation after completion of the monitored reaction; and (2), preparation of2-amino-3,5-dichloro-N-isopropylbenzamide: adding dichlorohydantoin slowly to the reaction solution of the step (1), controlling the reaction temperature at 20-40 DEG C, monitoring the reaction progress in the liquid phase, performing vacuum concentration on the reaction system after completion of the reaction, performing suction filtration, washing the solid with a little hot water, and performing beating with methanol so as to obtain a white compound. According to the method for preparing 2-amino-3,5-dichloro-N-isopropylbenzamide, a novel chlorination method is adopted so as to obtain 2-amino-3,5-dichloro-N-isopropylbenzamide efficiently, and the preparation method has simple post-treatment and a high total yield.

Description

technical field [0001] The invention belongs to the technical field of pesticide intermediate synthesis, and in particular relates to a method for preparing 2-amino-3,5-dichloro-N-isopropylbenzamide. Background technique [0002] 2-Amino-3,5-dichloro-N-isopropylbenzamide is a key intermediate in the synthesis of 3,5-dihalobenzamide insecticides. 3,5-Dihalogenated benzamide insecticides were invented by Qingdao University of Science and Technology, and have similar properties to 2-amino-3-methyl-5-chlorobenzamide insecticides (produced by Japan Pesticide Company, USA A new type of pesticide developed by DuPont and Bayer Pesticide Science and Technology, the trade name is "Kangkuan") active potential high-efficiency and low-toxicity active compound. Due to existing process limitations, the cost of intermediate 2-amino-3-methyl-5-chlorobenzamide is very high, and the cost of 2-amino-3,5-dichloro-N-isopropylbenzamide Only 1 / 8~1 / 10 of the former, so it has a very large cost adv...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C237/30
CPCC07C231/12C07C231/02C07C237/30
Inventor 黄轩
Owner 中翌科技有限公司
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