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Synthesis method for indoxacarb intermediate chloroformyl [4-(trifluoromethoxy) phenyl] methyl carbamate

A technology of methyl carbamate and trifluoromethoxyaniline, which is applied in the field of pesticide preparation, can solve the problems of large overflow of phosgene, large amount of waste water, high risk, etc., to reduce production costs, simplify operation steps, and shorten the reaction cycle effect

Active Publication Date: 2019-03-29
山东华阳农药化工集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the existing technology, whether the slurry is added dropwise to triphosgene or diphosgene, or the toluene solution of phosgene is added dropwise to the slurry, the rate of addition needs to be very slow, otherwise the phosgene is very easy to overflow in large quantities, and there is Higher risk, and the two-step reaction requires post-processing steps such as washing and layering, resulting in more waste water and a longer reaction cycle

Method used

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  • Synthesis method for indoxacarb intermediate chloroformyl [4-(trifluoromethoxy) phenyl] methyl carbamate
  • Synthesis method for indoxacarb intermediate chloroformyl [4-(trifluoromethoxy) phenyl] methyl carbamate

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preparation example Construction

[0026] The invention provides a method for synthesizing methyl chloroformyl [4-(trifluoromethoxy)phenyl]carbamate, an indoxacarb intermediate, and the specific steps are:

[0027] Step 1: Pass phosgene into the toluene solution at -5-5°C, then add the toluene solution of p-trifluoromethoxyaniline dropwise, and remove excess gas after the reaction solution is kept warm.

[0028] Step 2: Add an acid-binding agent to the reaction solution, add methyl chloroformate dropwise at -10-10°C, control the temperature of the reaction solution to not exceed 15°C for the reaction, and keep the reaction solution warm after the reaction.

[0029] Step 3: After the reaction solution is kept warm, it is washed with water, concentrated, crystallized and dried to obtain a white solid product.

[0030] At the same time, it provides an indoxacarb intermediate, methyl chloroformyl [4-(trifluoromethoxy)phenyl] carbamate, which is prepared by the above synthesis method.

Embodiment 1

[0033] Step 1: Put an appropriate amount of toluene into a 500ml reaction bottle, cool down to -5-0°C, and pass phosgene into the solution. Phosgene is generated according to a conventional method, and the mass content is: COCl 2 91.9%, Cl 2 0.13%, CO 2 3.01%, CO 3.96%, N 2 0.6%, O 2 0.1%, impurity 0.3%,

[0034] After passing through phosgene for 0.25h, add dropwise a toluene solution containing 0.3mol p-trifluoromethoxyaniline. After 1h, the dropwise addition is completed. Keep the temperature of the reaction solution at 0-5°C and keep it warm for 1h.

[0035] After the heat preservation is completed, keep the temperature of the reaction solution, and pass nitrogen to drive out excess phosgene and generated hydrogen chloride;

[0036] Step 2: Cool the reaction solution to -10--5°C, add 0.6 mol of triethylamine, add dropwise 0.33 mol of methyl chloroformate for 1 hour, keep the temperature of the reaction solution not exceeding 0°C during the dropwise addition,

[0...

Embodiment 2

[0043] Step 1: Put an appropriate amount of toluene into a 500ml reaction bottle, cool down to -5-0°C, and pass phosgene into the solution. Phosgene is generated according to a conventional method, and the mass content is: COCl 2 92.9%, Cl 2 0.13%, CO 2 2.01%, CO 3.56%, N2 0.8%, O 2 0.3%, impurity 0.3%,

[0044] After passing through phosgene for 0.5h, add dropwise a toluene solution containing 0.3mol p-trifluoromethoxyaniline. After 1.5h, the dropwise addition is completed. Keep the temperature of the reaction solution at 3-8°C and keep it warm for 1.5h.

[0045] After the heat preservation is completed, keep the temperature of the reaction solution, and pass nitrogen to drive out excess phosgene and generated hydrogen chloride;

[0046] Step 2: Cool down the reaction liquid to -5-0°C, add N,N-diisopropylethylamine and triethylamine in total 0.65mol, drop 0.37mol methyl chloroformate for 1.5h, keep the reaction during the dropwise addition The temperature of the liqu...

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Abstract

The invention discloses a synthesis method for an indoxacarb intermediate chloroformyl [4-(trifluoromethoxy) phenyl] methyl carbamate and relates to the field of pesticide preparation. A process routeof acylating p-trifluoromethoxy aniline with phosgene and then reacting with methyl chloroformate is adopted: triggering reaction of p-trifluoromethoxy aniline and phosgene under low temperature, thereby acquiring p-trifluoromethoxy phenylcarbamyl chloride; triggering reaction of p-trifluoromethoxy phenylcarbamyl chloride and methyl chloroformate, thereby acquiring chloroformyl [4-(trifluoromethoxy) phenyl] methyl carbamate. In the invention, phosgene can directly react with p-trifluoromethoxy aniline; no catalyst is required; the steps of water shearing before action, water washing after reaction, and the like, in the prior art are avoided; the flow of phosgene introduced into the reaction system can be controlled; reaction process can be controlled; high-corrosivity sodium cyanide or low-stability mixed alkali used as an initiator in the prior art can be avoided; operation steps are simplified; reaction period is shortened; production cost is lowered; the synthesis method is easy for industrialization.

Description

technical field [0001] The invention discloses a synthesis method and relates to the field of pesticide preparation, in particular to a synthesis method of indoxacarb intermediate chloroformyl [4-(trifluoromethoxy)phenyl]carbamate. Background technique [0002] Indoxacarb (C 22 h 17 CIF 3 N 3 o 7 , common name indoxacarb) is a kind of high-efficiency, low toxicity novel oxadiazine class sodium channel blocking formulation insecticide developed by DuPont Company of the United States at the end of last century. It has a wide insecticidal spectrum and quick effect. Plutella xylostella, cotton bollworm and other resistant pests have excellent control effects, and have no cross-resistance with other insecticides, and have no carcinogenic, teratogenic and mutagenic effects. Indoxacarb is one of the candidates for the large-scale demonstration and promotion of the Ministry of Agriculture in my country to replace highly toxic and high-residue pesticides. [0003] Methyl chloro...

Claims

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Application Information

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IPC IPC(8): C07C271/66C07C269/04C07C271/04C07C269/00
CPCC07C269/00C07C269/04C07C271/04C07C271/66
Inventor 孙绪兵李和娟闫新华李振兴陈永平王同涛高文
Owner 山东华阳农药化工集团有限公司
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