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Method for producing 2-nitro-p-methylsullfonyl benzoic acid

A technology of thiamphenicol benzoic acid and its production method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of insufficient purity of thiamphenicol benzoic acid, high production cost, etc., and achieve high yield , high degree of controllability, clear and definite process route

Inactive Publication Date: 2010-12-22
ANJI HAOSEN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the o-nitro p-thiamphenicol benzoic acid not only production cost is big but also makes the o-nitro p-thiamphenicol benzoic acid purity not enough by this method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The production method of 2-nitro-p-thiamphenicol benzoic acid, concrete steps are as follows:

[0026] ①Add 180 parts of concentrated sulfuric acid with a mass fraction of 90% to the reaction kettle, then add 30 parts of p-thymphenyltoluene, and cool to 0-4°C;

[0027] ② Add a mixed acid consisting of concentrated sulfuric acid with a mass fraction of 90% and concentrated nitric acid with a mass fraction of 60% in the ratio of 1:0.5 to the above reaction system, and keep the temperature change in the reaction system within 4°C during the addition process; add the mixed acid Then heat up to 20-30°C and stir rapidly;

[0028] ③ Cool the above reaction system to below 20°C, add 100 parts of water, add 2 parts of potassium permanganate, then raise the temperature in the reaction kettle to 50-60°C, add 70 parts of potassium dichromate dihydrate, 120 Potassium dichromate solution made of water, when adding potassium dichromate solution, control the temperature change in the ...

Embodiment 2

[0032] The production method of 2-nitro-p-thiamphenicol benzoic acid, concrete steps are as follows:

[0033] ① Add 181 parts of concentrated sulfuric acid with a mass fraction of 92% in the reaction kettle, then add 31 parts of p-thymphenyltoluene, and cool to 0-4°C;

[0034] ② Add a mixed acid consisting of concentrated sulfuric acid with a mass fraction of 92% and concentrated nitric acid with a mass fraction of 61% in a ratio of 1:0.6 to the above reaction system, and keep the temperature change in the reaction system within 4°C during the addition process; add the mixed acid Then heat up to 20-30°C and stir rapidly;

[0035] ③ Cool the above reaction system to below 20°C, add 102 parts of water, add 2 parts of potassium permanganate, then raise the temperature in the reaction kettle to 50-60°C, add 71 parts of potassium dichromate dihydrate, 121 Potassium dichromate solution made of water, when adding potassium dichromate solution, control the temperature change in the r...

Embodiment 3

[0039] The production method of 2-nitro-p-thiamphenicol benzoic acid, concrete steps are as follows:

[0040] ①Add 182 parts of concentrated sulfuric acid with a mass fraction of 94% to the reaction kettle, then add 32 parts of p-thymphenyltoluene, and cool to 0-4°C;

[0041] ② Add a mixed acid consisting of concentrated sulfuric acid with a mass fraction of 94% and concentrated nitric acid with a mass fraction of 62% in a ratio of 1:0.7 to the above reaction system, and keep the temperature change in the reaction system within 4°C during the addition process; add the mixed acid Then heat up to 20-30°C and stir rapidly;

[0042] ③ Cool the above reaction system to below 20°C, add 104 parts of water, add 3 parts of potassium permanganate, then raise the temperature in the reaction kettle to 50-60°C, add 72 parts of potassium dichromate dihydrate, 122 Potassium dichromate solution made of water, when adding potassium dichromate solution, control the temperature change in the reac...

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Abstract

The invention relates to a method for producing 2-nitro-p-methylsullfonyl benzoic acid. The method comprises the following steps of: dissolving methyl p-tolyl sulfone with concentrated sulfuric acid; oxidizing methyl tolyl sulfone into 2-nitro methyl p-tolyl sulfone with mixed acid of concentrated nitric acid and concentrated sulfuric acid at low temperature; oxidizing the 2-nitro methyl p-tolyl sulfone into 2-nitro-p-methylsullfonyl benzoic acid with potassium permanganate at a proper temperature; and then purifying the product respectively with sodium hydroxide and hydrochloric acid. The whole reaction line is clear and definite, has high operable degree and is particularly suitable for the industrial production; and moreover, the reaction product is not easy to pollute the environment, and the yield and the purity are high. The invention belongs to the technical field of fine chemical industry.

Description

technical field [0001] The invention relates to a production method of 2-nitro-p-thiamphenicol benzoic acid, which belongs to the technical field of fine chemicals. Background technique [0002] 2-Nitro-p-thiamphenicol benzoic acid is an important pharmaceutical intermediate. The preparation of this type of benzoic acid containing multiple electron-withdrawing groups usually requires the use of strong oxidant nitric acid to oxidize the toluene of the corresponding substituents. Since the toluene containing electron-withdrawing groups is difficult to oxidize, it can only be carried out under the catalysis of vanadium pentoxide. For example, Unitde States Patent 5,424,481 introduces the method of oxidation of o-nitro-p-thiamphenicol benzoic acid with nitric acid under the catalysis of vanadium pentoxide, the product purity can reach more than 90%, and the yield is more than 80%. Although the yield of this method is relatively high, due to the nitrogen dioxide gas produced dur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/44C07C315/04
Inventor 徐淑琴张根法吴继斌
Owner ANJI HAOSEN PHARMA
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