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Method for preparing 2-amido-5-thiobenzoic acid

A technology of thiobenzoic acid and halogenated benzoic acid, which is applied in thiol preparation, thioether preparation, organic chemistry and other directions, can solve the problems of long synthesis method steps, many post-processing processes, low efficiency and the like, and achieves less environmental pollution. , the process is simple, the effect of high chemical yield

Inactive Publication Date: 2014-04-23
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome above-mentioned deficiency, the present invention aims to provide a kind of cost low, and yield is high, and step is short, the preparation method of 2-amino-5-thiobenzoic acid that aftertreatment is simple, has solved synthetic method step is long, and efficiency is low, Many problems in post-processing

Method used

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  • Method for preparing 2-amido-5-thiobenzoic acid
  • Method for preparing 2-amido-5-thiobenzoic acid
  • Method for preparing 2-amido-5-thiobenzoic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Embodiment 1: prepare 2-amino-5-mercaptobenzoic acid with 2-nitro-5-chlorobenzoic acid

[0039] (1) Add 40 g of 2-nitro-5-chlorobenzoic acid and 60 mL of deionized water into a reaction vessel at a temperature of -10~10 °C, and add 60 mL of 4 mol / L NaOH aqueous solution to the mixture under stirring , so that 2-nitro-5-chlorobenzoic acid was completely dissolved. Na 2 S·9H 2 Dissolve 96 g of O solid in 100 mL of water, slowly pour it into the above solution, raise the reaction temperature to 50°C and stir, and strictly control the reaction temperature range between 45°C and 55°C.

[0040] (2) After reacting for 8 hours, continue to add Na to the reaction system 2 S·9H 2 O solid 96 g, heated up to 100 ° C, stirred for 5 hours, the color of the solution gradually changed from dark brown to dark red.

[0041] (3) After the reaction, cool down to room temperature, slowly add concentrated hydrochloric acid dropwise to the deep red solution to adjust the pH to 5, at this...

Embodiment 2

[0043] Example 2: Preparation of 2-amino-5-mercaptobenzoic acid from 2-nitro-5-fluorobenzoic acid

[0044] 37 g of 2-nitro-5-fluorobenzoic acid was added in a reaction vessel at a temperature of -10 ~ 10°C, and the target product 2-amino-5-mercaptobenzoic acid was obtained according to the method described in Example 1, with a yield of 90 %.

Embodiment 3

[0045] Example 3: Preparation of 2-amino-5-mercaptobenzoic acid from 2-nitro-5-bromobenzoic acid

[0046] 49 g of 2-nitro-5-bromobenzoic acid was added in a reaction vessel at a temperature of -10 to 10°C, and the target product 2-amino-5-mercaptobenzoic acid was obtained according to the method described in Example 1, with a yield of 92% .

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Abstract

The invention discloses a method for preparing 2-amido-5-thiobenzoic acid. The method is characterized by comprising the following steps: taking 2-nitro-5-halogen-benzoic acid as a raw material, performing the nucleophilic substitution reaction of the 2-nitro-5-halogen-benzoic acid and sulfur-bearing reagents in alkaline aqueous solutions firstly, wherein the mole ratio of the 2-nitro-5-halogen-benzoic acid to the sulfur-bearing reagents is 1:(1-4), then adding nitro reductants to generate reduction reaction, and finishing preparing the 2-amido-5-thiobenzoic acid through two-step conversion in the same container. The method has the advantages that the raw materials are easy to obtain, environment pollution is small (water is used as a reaction solvent), a process is simple, chemical yield is high, aftertreatment is simple, the practicability of the preparation method is strong, cheap inorganic salt Na2S (sodium sulfide) is used as a reductant for nitro-reduction, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 2-amino-5-thiobenzoic acid, which belongs to the technical field of preparation of fine chemical products. Background technique [0002] 2-Amino 5-thiobenzoic acid compounds are widely used in the synthesis and production of biological, pharmaceutical and pesticide intermediates, such as the synthesis of Ellman's reagent for detecting sulfhydryl content, and the preparation of pharmaceutically active sulfone compounds ( J. Med. Chem. 1995, 38 , 3547-3557), thioether-substituted benzopyrazolones ( J. Med. Chem. 1991, 34, 2209-2218; WO2008044688 (A1); J. Med. Chem. 2004, 47, 6730-6739), sulfur-containing phenazine active compounds ( J. Antibio. 1995, 48 , 1081-1085), a thioether aminobenzyl alcohol with inhibitory serotonin transport activity ( J. Med. Chem. 2008, 51, 271–281), and the preparation of several sulfa drugs. And the compound containing this structure has good biological activity (...

Claims

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Application Information

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IPC IPC(8): C07C323/63C07C319/12C07C319/20
Inventor 高文超田俊
Owner TAIYUAN UNIV OF TECH