Method for preparing 4-trifluoro-methoxy phenyl carbamate

A technology of methyl carbamate and trifluoromethoxybenzene, which is applied in the field of preparation of methyl 4-trifluoromethoxyphenyl carbamate, can solve problems such as not meeting the requirements of green chemistry, and achieves simple operation, good yield

Inactive Publication Date: 2009-12-16
WENZHOU UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Methyl chloroformate is a highly toxic compound in the reaction. In addition, N, N-diethylaniline is generally used as a solvent in this reaction, and a large amount of by-products are produced in the reaction, which does not meet the requirements of green chemistry.

Method used

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  • Method for preparing 4-trifluoro-methoxy phenyl carbamate
  • Method for preparing 4-trifluoro-methoxy phenyl carbamate
  • Method for preparing 4-trifluoro-methoxy phenyl carbamate

Examples

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Effect test

Embodiment 1

[0028] Under normal pressure, first add 10.80mL (0.12mol) of dimethyl carbonate and 0.8856g of zinc acetate catalyst to a 50mL three-necked flask, connect the flask to a condensation reflux column, and feed N into the system. 2 , stirred magnetically and raised the temperature to about 170°C and maintained it for a period of time, then added 2.71mL (0.02mol) of 4-trifluoromethoxyaniline and raised the temperature to 180°C, then started timing. where n (4-三氟甲氧基苯胺) : n (碳酸二甲酯) =1:6. After reacting for 10 hours, let it stand for 2 hours, and the filtrate was washed with 15mL CH 2 Cl 2 After refluxing at 55°C for a period of time, extraction was carried out, and the extract was left to stand at room temperature for 24 hours, then spin-dried, and then further purified by column chromatography (300-400 mesh silica gel as a stationary phase), and then extracted with petroleum ether and ethyl acetate. Ester as eluent (V (石油醚) :V (乙酸乙酯) =3:1), a pale yellow solid was isolated wit...

Embodiment 2

[0030] Under normal pressure, first add 7.20mL (0.08mol) of dimethyl carbonate and 0.8856g of zinc acetate catalyst into a 50mL three-necked flask, connect the flask to a condensation reflux column, and pass people N into the system. 2 , stirred magnetically and raised the temperature to about 170°C and maintained it for a period of time, then added 2.71mL (0.02mol) of 4-trifluoromethoxyaniline and raised the temperature to 180°C, then started timing. where n (4-三氟甲氧基苯 胺) : n (碳酸二甲酯) =1:4. After reacting for 7 hours, 3.60 mL (0.04 mol) of dimethyl carbonate was added to make the molar ratio of 4-trifluoromethoxyaniline to dimethyl carbonate finally 1:6. Continue to react until 10 hours to stop the reaction, let it stand for 2 hours, and the filtrate is washed with 15mL CH 2 Cl 2 After refluxing at 55°C for a period of time, extraction was carried out, and the extract was left to stand at room temperature for 24 hours, then spin-dried, and then further purified by column c...

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Abstract

The invention belongs to the technical field of preparing pesticide intermediates and pharmaceutical intermediates, in particular to a method for preparing 4-trifluoro-methoxy phenyl carbamate. The method adopts 4-trifluoro-methoxyaniline as a starting raw material, and uses dimethyl carbonate as methoxycarbonyl reagent and solvent; and under normal pressure, the method utilizes catalyst to carry out carbonylation reaction to obtain the product. The invention aims at providing the method for preparing the 4-trifluoro-methoxy phenyl carbamate, which has low toxicity of raw materials, less pollution and easy reaction control. Compared with the prior art, the invention has the advantages of simple operation steps, higher yield, high product quality, low corrosion of raw materials, less environmental pollution, etc.

Description

technical field [0001] The invention belongs to the technical field of preparation of pesticide intermediates and pharmaceutical intermediates, and in particular relates to a preparation method of methyl 4-trifluoromethoxyphenylcarbamate. Background technique [0002] Methyl 4-trifluoromethoxyphenylcarbamate is the precursor for the synthesis of the key intermediate of indoxacarb (chlorocarbonyl) methyl 4-trifluoromethoxyphenylcarbamate, and it is also the production of other important pharmaceutical intermediates. At present, the main method of synthesis of this product is: [0003] [0004] Methyl chloroformate is a highly toxic compound in the reaction. In addition, N, N-diethylaniline is generally used as a solvent in this reaction, and a large amount of by-products are produced in the reaction, which does not meet the requirements of green chemistry. Contents of the invention [0005] In order to overcome the deficiencies in the preparation method of existing 4-tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/28C07C269/04B01J31/04
Inventor 胡新根陈帆余生朱玉青潘万成高鋆
Owner WENZHOU UNIVERSITY
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