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Methods for synthesizing isatoic anhydride and N-isopropyl-2-aminobenzamide

A synthesis method and technology of isatoic anhydride are applied in the synthesis of N-isopropyl-2-aminobenzamide and the synthesis field of isatoic anhydride, which can solve the problem of unstable quality of bentazon preparations, increasing operation steps, prolonging Production cycle and other problems, to achieve the effect of shortening production cycle, reducing operation steps, and cleaning the synthesis process

Active Publication Date: 2011-02-16
HEFEI XINGYU CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since isatoic anhydride is generally synthesized in an aqueous medium, it is necessary to extract, purify, and dry the isatoic anhydride before performing the amidation reaction in an organic solvent, which increases the operation steps and prolongs the production cycle.
And existing isatoic anhydride product purity is lower, and the impurity such as the anthranilic acid that contains also exists in intermediate N-isopropyl-2-aminobenzamide and final product bendazone, causes the quality of bendazone preparation Unstable, long-term storage will produce precipitation and turbidity

Method used

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  • Methods for synthesizing isatoic anhydride and N-isopropyl-2-aminobenzamide
  • Methods for synthesizing isatoic anhydride and N-isopropyl-2-aminobenzamide
  • Methods for synthesizing isatoic anhydride and N-isopropyl-2-aminobenzamide

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preparation example Construction

[0024] The invention provides a kind of synthetic method of isatoic anhydride, comprising:

[0025] Add bis(trichloromethyl)carbonate solution dropwise to the anthranilic acid solution, and reflux reaction to obtain isatoic anhydride.

[0026] The invention uses anthranilic acid and bis(trichloromethyl)carbonate as raw materials to react in an organic solvent to generate isatoic anhydride.

[0027] Anthranilic acid has a structure of formula (II), which is relatively similar to the structure of isatoic anhydride having a structure of formula (I).

[0028]

[0029] Bis (trichloromethyl) carbonate, also known as solid phosgene or triphosgene, the chemical formula is C 3 o 3 Cl 6 , low toxicity, relatively safe during transportation, storage and use.

[0030] According to the present invention, at first prepare anthranilic acid solution and two (trichloromethyl) carbonate solution, specifically comprise the following steps:

[0031] Anthranilic acid is mixed with an organ...

Embodiment 1

[0051] Add 20 g of commercially available anthranilic acid and 150 mL of ethylene dichloride with a purity of 98% in a 500 mL four-necked bottle equipped with a stirrer, a thermometer and a circulating condensing device, turn on the stirrer and a circulating condensing device, and heat up to 68 ℃, stirred until anthranilic acid was completely dissolved to obtain anthranilic acid solution; 16 g of commercially available bis(trichloromethyl)carbonate was dissolved in 40mL of dichloroethane to obtain bis(trichloromethyl)carbonic acid Ester solution; the bis(trichloromethyl)carbonate solution was slowly added dropwise to the anthranilic acid solution for 2 hours, then the temperature was raised to 75° C. for reflux reaction for 2 hours to obtain isatoic anhydride solution. After cooling down to room temperature, the isatoic anhydride solution was suction-filtered and weighed 22.7 g after drying. The dried product was subjected to liquid chromatography measurement, wherein the isat...

Embodiment 2

[0053] Add 20 g of commercially available anthranilic acid and 150 mL of ethylene dichloride with a purity of 98% in a 500 mL four-necked bottle equipped with a stirrer, a thermometer and a circulating condensing device, turn on the stirrer and a circulating condensing device, and heat up to 68 ℃, stirred until anthranilic acid was completely dissolved to obtain anthranilic acid solution; 16 g of commercially available bis(trichloromethyl)carbonate was dissolved in 40mL of dichloroethane to obtain bis(trichloromethyl)carbonic acid Ester solution; slowly drop the bis(trichloromethyl)carbonate solution into the anthranilic acid solution for 2 hours, then heat up to 80° C. for reflux reaction for 2 hours to obtain isatoic anhydride solution;

[0054] The temperature of the isatoic anhydride solution was lowered to 55°C, and 12 g of isopropylamine was slowly added dropwise for 2 hours, and then kept for 1 hour to obtain N-isopropyl-2-aminobenzamide solution, and the solution was su...

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Abstract

The invention provides a method for synthesizing isatoic anhydride, comprising the steps of: dropwise adding a di(trichloromethyl) carbonic ester solution into an o-aminobenzoic acid solution, refluxing for reaction to obtain the isatoic anhydride. The invention further also provides a method for synthesizing N-isopropyl-2-aminobenzamide, comprising the steps of: a) dropwise adding the di(trichloromethyl) carbonic ester solution into the o-aminobenzoic acid solution, and refluxing for reaction to obtain an isatoic anhydride solution; and b) dropwise adding isopropamide into the isatoic anhydride solution, and reacting to obtain the N-isopropyl-2-aminobenzamide. After o-aminobenzoic acid and di(trichloromethyl) carbonic ester react in an organic solvent to generate the isatoic anhydride, the N-isopropyl-2-aminobenzamide can be obtained by directly adding the isopropamide for amidation, without carrying out the steps of extraction, purification, drying and the like on the isatoic anhydride, therefore, operation steps are reduced, production cycle is shortened, and industrialized production is easy to realize.

Description

technical field [0001] The invention relates to the technical field of pesticide intermediate compounds, in particular to a synthesis method of isatoic anhydride and a synthesis method of N-isopropyl-2-aminobenzamide. Background technique [0002] Isatoic anhydride, also known as etoric anhydride, N-carboxy-anthranilic anhydride, carboxy-anthranilic anhydride, English name is 4H-3, 1-benzoxazine-2, 4(1H)-dione, CAS registration number is 118 -48-9, molecular formula is C8H5NO3, relative molecular weight is 163.13, and structural formula is as shown in (I): [0003] [0004] Isatoic anhydride can react with both electrophile and nucleophile. It is a useful chemical intermediate widely used in agricultural chemicals, dyes, pigments, spices, flavors, medicines, blowing agents, barrier Synthesis of fuel and other fine chemical products. [0005] The prior art discloses a variety of synthetic methods for isatoic anhydride, such as dissolving anthranilic acid in hot water and...

Claims

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Application Information

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IPC IPC(8): C07C237/30C07D265/26C07C231/10
Inventor 何普泉姚海波王龙刘美盛王兰兰赵国霞
Owner HEFEI XINGYU CHEM
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