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Synthetic method for trimethoprim drug intermediate-p-hydroxy benzaldehyde

A technology of p-hydroxybenzaldehyde and trimethoprim, which is applied in the field of synthesis of trimethoprim drug intermediate p-hydroxybenzaldehyde, can solve the problems of rarely used alone, and bacteria are prone to drug resistance, so as to reduce intermediate link, reduce the reaction temperature and reaction time, and increase the effect of reaction yield

Inactive Publication Date: 2016-06-01
CHENGDU ZHONGHENG HUATIE TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Trimethoprim is a broad-spectrum antibacterial drug, the antibacterial spectrum is similar to that of sulfa drugs, and it can inhibit dihydrofolate reductase, but bacteria are prone to drug resistance, so it is rarely used alone

Method used

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  • Synthetic method for trimethoprim drug intermediate-p-hydroxy benzaldehyde

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example 1

[0014] (i) Add 0.17mol of p-aminobenzaldehyde (2) and 150ml of water into a reaction vessel with a volume of 800mL, slowly add 50mL of concentrated phosphoric acid with a mass fraction of 50%, control the temperature of the solution to rise to 80°C, and generate phosphate to obtain Suspension, cool the solution to 15°C, slowly add 0.25mol of sodium bisulfite dissolved in 100ml of aqueous solution dropwise, control the stirring speed at 100rpm during the dropwise addition, and test the end point with potassium iodide test paper;

[0015] (ii) Control the temperature of the solution at 30°C, let it stand for 20min, add 5g of urea, control the temperature of the solution to rise gradually, after a large amount of gas escapes, heat the solution to 90°C, keep it for 10min, decolorize with molecular sieve, filter while hot, filter The cake was washed with ether solvent, the filtrate and the washing liquid were combined, and the solid was precipitated after the temperature was lowered...

example 2

[0017] (i) Add 0.17mol of p-aminobenzaldehyde (2) and 180ml of water into a reaction vessel with a volume of 900mL, slowly add 50mL of concentrated phosphoric acid with a mass fraction of 60%, control the temperature of the solution to rise to 90°C, and generate phosphate, and obtain Suspension, cool the solution to 17°C, slowly add 0.25mol of sodium bisulfite dissolved in 100ml of aqueous solution dropwise, control the stirring speed at 200rpm during the dropwise addition, and test the end point with potassium iodide test paper;

[0018] (ii) Control the temperature of the solution at 30°C, let it stand for 20min, add 5g of urea, control the temperature of the solution to rise gradually, after a large amount of gas escapes, heat the solution to 92°C, keep it for 10min, decolorize with molecular sieve, filter while hot, filter The cake was washed with acetone solvent, the filtrate and the washing liquid were combined, and the solid was precipitated after the temperature was low...

example 3

[0020] (i) Add 0.17mol of p-aminobenzaldehyde (2) and 200ml of water into a reaction vessel with a volume of 1000mL, slowly add 50mL of concentrated phosphoric acid, control the temperature of the solution to rise to 95°C, and generate phosphate to obtain a suspension, and cool the solution To 20°C, slowly add 0.25mol of sodium bisulfite dissolved in 100ml of aqueous solution dropwise, control the stirring speed at 300rpm during the dropwise addition, and test the end point with potassium iodide test paper;

[0021] (ii) Control the temperature of the solution at 30°C, let it stand for 20min, add 5g of urea, control the temperature of the solution to rise gradually, after a large amount of gas escapes, heat the solution to 95°C, keep it for 10min, decolorize with molecular sieve, filter while hot, filter The cake was washed with ethyl acetate solvent, the filtrate and the washing liquid were combined, and a solid was precipitated after the temperature was lowered, and the solid...

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Abstract

The invention discloses a synthetic method for a trimethoprim drug intermediate-p-hydroxy benzaldehyde. The method comprises the following steps: (i) adding 0.17mol of p-aminotenzaldehyde (2) and 150-200ml of water into a reaction container with the volume of 800-1,000mL, slowly adding 50mL of strong phosphoric acid, controlling the temperature of a solution to be increased to 80-95 DEG C, generating phosphate, obtaining a suspension liquid, cooling the solution to 15-20 DEG C, slowly dropwise adding 0.25mol of sodium hydrogen sulfite, performing dissolution in 100ml of an aqueous solution, controlling the stirring speed to be 100-300rpm in the dropwise adding process, and testing a termination point by potassium iodide test paper; and (ii) controlling the temperature of the solution to be 30 DEG C, standing for 20 minutes, adding 5g of urea, controlling the temperature of the solution to be gradually increased, after a large amount of gas escapes, heating the solution to 90-95 DEG C, keeping the temperature for 10 minutes, performing decolorization by using a molecular sieve, immediately filtering, washing a filter cake with a solvent, combining a filter liquor with a washing liquid, after the temperature is reduced, separating out solid, adding the solid into a sodium chloride solution for recrystallization, filtering, and drying to obtain p-hydroxy benzaldehyde.

Description

technical field [0001] The invention relates to a method for synthesizing trimethoprim drug intermediate p-hydroxybenzaldehyde. Background technique [0002] Trimethoprim is a broad-spectrum antibacterial drug with a similar antibacterial spectrum to sulfonamides. It has the effect of inhibiting dihydrofolate reductase, but bacteria are prone to drug resistance and are rarely used alone. Sulfonamides inhibit dihydrofolate synthase. The combination of the two can double block the folic acid metabolism of bacteria, thus greatly improving the antibacterial effect (several times to dozens of times), so it is called a sulfonamide synergist, and can reduce the emergence of drug-resistant strains . p-Hydroxybenzaldehyde is an intermediate of trimethoprim medicine, the advantages and disadvantages of its synthesis method are of great economic significance for improving the quality of medicine synthesis products and reducing the content of by-products. Contents of the invention ...

Claims

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Application Information

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IPC IPC(8): C07C45/64C07C47/565
CPCC07C45/64C07C245/20
Inventor 彭响亮
Owner CHENGDU ZHONGHENG HUATIE TECH CO LTD
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