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Preparation method of 2-nitryl-4-thiamphenicol benzoic acid

A technology of methylsulfonyl benzoic acid and methylsulfonyl benzonitrile, which is applied in the field of preparation of 2-nitro-4-methylsulfonyl benzoic acid, can solve problems such as complicated reaction steps, and achieves high product purity, simple process, The effect of mild reaction conditions

Active Publication Date: 2010-01-20
NUTRICHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] In this method, the carboxyl group needs to be protected first during the reaction. After the methylsulfone group is introduced on the benzene ring, the carboxyl group is deprotected. The reaction steps are cumbersome; In the process of sulfone group, it reacts with carboxyl group to produce by-products

Method used

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  • Preparation method of 2-nitryl-4-thiamphenicol benzoic acid
  • Preparation method of 2-nitryl-4-thiamphenicol benzoic acid
  • Preparation method of 2-nitryl-4-thiamphenicol benzoic acid

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preparation example Construction

[0019] According to the present invention, the preparation method of described 2-nitro-4-thiamphenicol benzoic acid comprises the following steps:

[0020] (1) Under cyanidation reaction conditions and in the presence of a catalyst, 2-nitro-4-thiamphenicol chlorobenzene is reacted with cyanide to obtain 2-nitro-4-thiamphenicol benzonitrile;

[0021] (2) The 2-nitro-4-thiamphenicol benzonitrile obtained in the step (1) is subjected to a hydrolysis reaction.

[0022] The preparation route of 2-nitro-4-thiamphenicol benzoic acid provided by the invention can be represented by following reaction formula:

[0023]

[0024] According to the present invention, in the step (1), 2-nitro-4-thiamphenicol chlorobenzene and cyanide can react according to the stoichiometric ratio, in order to make the raw material 2-nitro-4-thiamphenicol chlorobenzene For a more complete reaction, the molar ratio of 2-nitro-4-thiamphenicol chlorobenzene to cyanide can be 1:1-2; preferably 1:1.1-1.5.

...

preparation Embodiment 1

[0052] This example is used to illustrate the preparation of 2-nitro-4-thiamphenicol chlorobenzene

[0053] (1) Add 174.8 grams (1.5 moles) of chlorosulfonic acid, 8.8 grams (0.15 moles) of sodium chloride and 150 milliliters of 1,2-dichloroethane in turn in the reaction flask; start stirring, heat and heat up to 55-60 ℃; then 1,2-dichloroethane solution (250 ml of 1,2-dichloroethane) containing 79.8 grams of o-chloronitrobenzene (0.5 mol, 99%) was added dropwise to the above-mentioned In the mixed solution; after the dropwise addition, keep warm for 5 hours, pour into 500 ml of ice-water mixture, stir, let stand, and separate the organic layer; dry the organic layer, and precipitate to obtain a light yellow solid 3-nitro- 4-Chlorobenzenesulfonyl chloride.

[0054] (2) Add 75.6 grams (0.6 moles) of anhydrous sodium sulfite, 400 milliliters of water and 84 grams (1.0 moles) of anhydrous sodium bicarbonate in the reaction flask in sequence; start stirring, heat to 70 ° C, and a...

Embodiment 1

[0056] This embodiment is used to illustrate the preparation of 2-nitro-4-thiamphenicol benzoic acid

[0057] (1) Under the protection of nitrogen gas, 130 grams of N-methylpyrrolidone and 22.8 grams (0.1 moles, 98.7%) of the 2-nitro-4-thiamphenicol prepared in Preparation Example 1 were successively added to the reaction flask Chlorobenzene, 11.1 grams (50 mmoles) of nickel bromide and 9.0 grams (0.1 moles) of cuprous cyanide, started stirring, heated to 160 ° C, stirred for 4 hours; then added 500 milliliters of ether and 150 milliliters of water, stirred, Stand to separate layers, dry the organic phase with anhydrous sodium sulfate, and remove the solvent to obtain 20.4 grams of solid;

[0058] (2) Add 20.4 grams of the solid obtained in step (1) and 50 milliliters of ethylene glycol successively to the reaction flask, start stirring, add 50 milliliters of water, 14.4 grams (0.36 moles) of sodium hydroxide, heat to 110° C., and keep warm 3 hours, cooled to room temperature...

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Abstract

The invention relates to a preparation method of 2-nitryl-4-thiamphenicol benzoic acid, which comprises the following steps: (1) reacting 2-nitryl-4-thiamphenicol benzoic acid with cyanide under the condition of carbonitriding reaction and in the existence of catalyst, and obtaining 2-nitryl-4-thiamphenicol cyanophenyl; and (2) hydrolyzing the 2-nitryl-4-thiamphenicol cyanophenyl obtained in the step 1. The product prepared by adopting the method has high productivity and high purity, and the invention has simple process, moderate reaction conditions and shorter reaction time; in addition, the invention also avoids the problems of serious equipment corrosion and environmental pollution caused by the use of strong acid and strong oxidizer, such as HNO3, H2SO4, H2O2, and the like.

Description

technical field [0001] The invention relates to a preparation method of 2-nitro-4-thiamphenicol benzoic acid. Background technique [0002] 2-nitro-4-thiamphenicol benzoic acid (NMSBA) is an important intermediate in the preparation of the herbicide mesotrione. Its structural formula is as shown in formula (I): [0003] [0004] About the synthetic method of 2-nitro-4-thiamphenicol benzoic acid, it has been reported in many patent documents, mainly divided into following two classes: [0005] 1. Using 2-nitro-4-thiamphenicol toluene as raw material, oxidize its methyl group into carboxyl group by various oxidants to prepare 2-nitro-4-thiamphenicol benzoic acid. The specific reaction formula is as follows: [0006] [0007] For example, CN1090843A discloses a preparation method of methanesulfonylbenzoic acid, which comprises the oxidation of methanesulfonyltoluene in sulfuric acid with nitric acid and air in the presence of vanadium or cobalt compounds. This method u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/44C07C315/04
Inventor 刘世禄李生学母灿先张政张永忠曹锦朱笑坤
Owner NUTRICHEM LAB CO LTD
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