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Synthetic method of methyl-4-(trifluoromethoxy) phenyl carbamate

A technology of trifluoromethoxyphenyl and methyl carbamate, which is applied in the preparation and application of fine chemical products, can solve the problems of unsuitability for large-scale production, increase the difficulty of reaction treatment, and limited source of raw materials, and achieve good application The prospect, the preparation method is simple and practical, and the effect of high economy

Inactive Publication Date: 2011-10-19
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current method for synthesizing this compound is to synthesize 4-trifluoromethoxyaniline and dimethyl carbonate as raw materials, but the by-products of this reaction are many and difficult to remove, the source of raw materials is limited, the synthesis process is complicated, and the yield is not high About 48%, and the process requirements are high, and product purification is difficult
There are also relevant literatures using ZrClO 2 / SiO 2 As a catalyst (Huaxue Shijie (2009), 50(4), 244-246, 233), but the post-treatment in this method is complicated, which undoubtedly increases the difficulty of the reaction, and the raw material cost of the product is high, which is not suitable for industrial mass production of

Method used

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  • Synthetic method of methyl-4-(trifluoromethoxy) phenyl carbamate

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Experimental program
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Effect test

Embodiment 1

[0019] A 150 mL four-necked flask equipped with a reflux and gas absorption device was added to 13.28g (0.075mol) of 4-trifluoromethoxyaniline, 6g of sodium hydroxide (0.15mol), 10ml of tetrahydrofuran and 100ml of water, and mixed well. React for 2h at a temperature of 15-20℃; then, warm to room temperature and stir for 30 minutes. Add 10ml of methyl chloroformate slowly at a rate of 10 seconds / drop, and stir for 6h at room temperature; after the reaction, the temperature is reduced to 0 ℃, the reaction was stirred for 30 minutes; the solid was suction filtered, washed with water, and dried to obtain 16-18g of the target product 4-trifluoromethoxyphenyl-carbamic acid methyl ester, conversion rate: 95%-99% 1 HNMR (400MHz, CDCl 3 ):δ(ppm) 3.67( s, 3H,CH 3 ), 8.0 (t, 1H, NH), 6.75 (d, 2H, ArH). 7.53 (d, 2H, ArH).

Embodiment 2

[0021] A 150 mL four-necked flask equipped with a reflux and gas absorption device was added to 13.28g (0.075 mol) of 4-trifluoromethoxyaniline, 15.9g (0.15 mol) of sodium carbonate, 10ml of dioxane and 100ml of water. After mixing uniformly, react for 2h at a temperature of 10-15℃; then, warm to room temperature and stir for 30 minutes. Add 10ml of methyl chloroformate slowly at a rate of 10 seconds / drop, and stir for 7h at room temperature; after the reaction is complete Cool down to 0℃, stir and react for 30 minutes; the solid is filtered by suction, washed with water, and dried to obtain the target product 4-trifluoromethoxyphenyl-carbamic acid methyl ester 16.5-18g, conversion rate: 95%-99% 1 HNMR (400 MHz, CDCl 3 ): δ (ppm) 3.67 (s, 3H, CH 3 ), 8.0 (t, 1H, NH), 6.75 (d, 2H, ArH). 7.53(d, 2H, ArH).

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Abstract

A synthetic method of methyl-4-(trifluoromethoxy) phenyl carbamate. Raw materials of 4-trifluoromethoxy-aniline, methyl chloroformate and alkalis and a mixed solvent of water and organic solvents are mixed and undergo directly a reaction to produce a product of methyl-4-(trifluoromethoxy) phenyl carbamate. The synthetic method comprises the following steps of 1, adding 4-trifluoromethoxy-aniline, sodium hydroxide, tetrahydrofuran and water into a container, mixing well and make the mixture undergo a reaction at a temperature of 0 to 5 DEG C for 2 hours, 2, heating the reaction products to room temperature and stirring for 30 minutes, adding slowly methyl chloroformate into the heated reaction products and stirring at room temperature for 6 to 7 hours, 3, cooling the reaction products obtained from the step 2 to 0 DEG C and stirring for 30 minutes, and 4, carrying out a suction filtration process for the reaction products obtained from the step 3 to collect solids, and washing and drying the solids to obtain desired products. The synthetic method has the advantages that the synthetic method is simple and practical, has a high efficiency and can realize an end product yield more than 95%; reagents adopted in synthesizing processes have the advantages of low toxicity, high economic efficiency, less side effects, less corrosion on equipment and less pollution on environment; and prices of raw materials are cheap thus a production cost is low and the synthetic method has a high economic efficiency and good application prospects.

Description

Technical field [0001] The invention relates to the field of preparation and application technology of fine chemical products, in particular to a method for synthesizing 4-trifluoromethoxyphenyl-carbamic acid methyl ester. Background technique [0002] 4-trifluoromethoxyphenyl-carbamic acid methyl ester, English name: methyl -4-(trifluoromethoxy) phenyl carbamate, methyl 4-(trifluoromethoxy) phenyl carbamate, is a kind of [0003] Colorless and transparent liquid easily soluble in water, alcohol, ether and other organic solvents, density: 1.32g / ml, boiling point: 130-132 [0004] ℃ (5mmHg), molecular formula: C 9 H 8 F 3 NO 3 , Molecular weight: 187, it is an intermediate of many important chemical products, among which the most important application is the relatively new pesticides cyflumizone and indoxacarb, cyflumizone (metaflumizone, BAS320I) is a German BASF company and Japanese pesticide A brand-new compound jointly developed by the company, which belongs to the semicarbazide ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/28C07C269/04
Inventor 徐凤波孔晓菲敖丽华张奉志董建兰
Owner NANKAI UNIV
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