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Method for preparing chlorocarbonyl[4-(trifluoromethoxy)phenyl] methyl carbamate

A technology of methyl carbamate and trifluoromethoxy, which is applied in the field of preparation of pharmaceutical intermediates, can solve the problems of large raw material moles, long reaction period, high risk and the like, and achieves shortened reaction period, reduced energy consumption, Residual reduction effect

Active Publication Date: 2014-07-23
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, sodium hydride has high chemical reactivity and can spontaneously ignite in humid air. When heated or in contact with moisture or acids, it will release heat and hydrogen to cause combustion and explosion. It can react strongly with oxidants to cause combustion or explosion. Hydroxide is formed with water, which is highly corrosive and dangerous, and the molar ratio of raw materials is relatively large, the reaction cycle is long, and the cost is high

Method used

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  • Method for preparing chlorocarbonyl[4-(trifluoromethoxy)phenyl] methyl carbamate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) Add 0.3mol p-trifluoromethoxyaniline, 0.45mol sodium hydroxide and toluene to a 1000ml clean and anhydrous reaction bottle, cool down to 10°C, add 0.63mol methyl chloroformate dropwise, and control the dripping for 3.5h;

[0024] (2) After the dropwise addition, slowly raise the temperature to 40°C, keep the temperature for 3 hours, wash with water, reflux and separate water until no water comes out;

[0025] (3) Add 1.05mol potassium methylate and potassium hydroxide mixed alkali (wherein, in terms of the molar ratio of pure substance, potassium methylate: potassium hydroxide=4:1) to the reaction solution obtained in step (2), heat up, fractionate to 110°C, react for 3.5h;

[0026] (4) Dissolve 0.9mol of Sangu Light in toluene, and control the temperature at 10°C;

[0027] (5) Add the reaction solution obtained in step (3) dropwise to the solution obtained in step (4), and control the reaction temperature to 15°C. After the dropwise addition, keep the reaction for...

Embodiment 2

[0031] (1) Add 0.3mol p-trifluoromethoxyaniline, 0.9mol sodium hydroxide and toluene to a 1000ml clean and anhydrous reaction bottle, cool down to -10°C, add 0.75mol methyl chloroformate dropwise, and control the dripping for 3.5h ;

[0032] (2) After the dropwise addition, slowly raise the temperature to 30°C, keep the temperature for 5 hours, wash with water, reflux and divide the water until no water comes out;

[0033] (3) Add 0.6mol potassium methylate and potassium hydroxide mixed alkali to the reaction solution obtained in step (2) (wherein, based on the molar ratio of pure substance, potassium methylate: potassium hydroxide=3:1), heat up, fractionate to 106°C, react for 2.5h;

[0034] (4) Dissolve 1.2mol of Sangu Light in toluene, and control the temperature at 0°C;

[0035] (5) Add the reaction solution obtained in step (3) dropwise to the solution obtained in step (4), and control the reaction temperature to 0°C. After the dropwise addition, keep the reaction for 2...

Embodiment 3

[0039] (1) Add 0.3mol p-trifluoromethoxyaniline, 0.6mol sodium hydroxide and toluene to a 1000ml clean and anhydrous reaction bottle, cool down to 0°C, add 0.54mol methyl chloroformate dropwise, and control the dripping for 3.5h;

[0040] (2) After the dropwise addition, slowly raise the temperature to 35°C, keep the temperature for 1.5 hours, wash with water, reflux and divide the water until no water comes out;

[0041] (3) Add 1.5mol potassium methylate and potassium hydroxide mixed alkali (wherein, in terms of the molar ratio of pure substance, potassium methylate: potassium hydroxide=4:1) to the reaction solution obtained in step (2), heat up, fractionate to 108℃, react for 5h;

[0042] (4) Dissolve 15mol of Sangu Light in toluene, and control the temperature at 5°C;

[0043] (5) Add the reaction solution obtained in step (3) dropwise to the solution obtained in step (4), and control the reaction temperature to 5°C. After the dropwise addition, keep the reaction for 1.5 ...

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Abstract

The invention relates to a method for preparing a drug intermediate and in particular relates to a method for preparing an intermediate chlorocarbonyl[4-(trifluoromethoxy)phenyl] methyl carbamate of an agricultural insecticide indoxacarb. Trifluoromethoxyaniline, methylchloroformate and triphosgene are mainly adopted as reactants, and the intermediate is prepared by using mixed alkali with higher safety. According to the method, the defect that a high-risk substance sodium hydride is needed to be adopted in the prior art is overcome, the operating environment is mild, the activity is improved through the mixed alkali process, and the hydrogen taking capacity is improved, so that the reaction speed is increased, the residues of raw materials are reduced, unnecessary side reactions are reduced, and the effects of shortening the reaction time and increasing the yield and product content are achieved; the method is greatly superior to an existing conventional preparation process, and a solid foundation is laid for preparing high-purity indoxacarb.

Description

technical field [0001] The invention relates to a preparation method of a class of pharmaceutical intermediates, in particular to a preparation method of methyl chlorocarbonyl[4-(trifluoromethoxy)phenyl]carbamate, an intermediate of the agricultural insecticide indoxacarb. Background technique [0002] Indoxacarb is an oxadiazine insecticide developed by DuPont in the United States in 1992. Its common name is indoxacarb, and its chemical name is (4aS)-7-chloro-2,5-dihydro-2-[[(methoxy Carbonyl)[4-(trifluoromethoxy)-phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester, The trade names include ammate (home run 30% water dispersant), vatar (hit 15% suspension concentrate) and so on. Its mechanism of action is a sodium channel inhibitor, which mainly blocks the sodium channel in the nerve cells of pests, leading to coordinated paralysis and eventual death of target pests. The pesticide enters the insect body through contact killing and inges...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/66C07C269/06
Inventor 李媛媛王鹏韦能春苑敬林戴荣华王平
Owner JINGBO AGROCHEM TECH CO LTD
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