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Aqueous phase synthesis method of probenecid

A probenecid and dipropylamine technology, applied in the field of organic chemical synthesis, can solve the problems of difficult disposal of waste water, restricted development, low yield, etc., and achieve the effects of simplifying operation, improving utilization rate, and high atom utilization rate

Active Publication Date: 2015-10-21
CHEM TECH ACAD OF SHANDONG PROVINCE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The process uses sodium dichromate or potassium permanganate to oxidize p-toluenesulfonamide, and the yield is low (less than 50%)
In addition, the wastewater containing chromium or manganese is difficult to dispose of, which seriously restricts the further development of this process

Method used

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  • Aqueous phase synthesis method of probenecid
  • Aqueous phase synthesis method of probenecid
  • Aqueous phase synthesis method of probenecid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] (1) Diazotization reaction

[0041] Take 68.6g of p-aminobenzoic acid (0.5mol), 250g of water and 127.4ml of hydrochloric acid (31%, 1.25mol) into a 2000ml three-neck flask, stir in an ice-water bath, cool down to 0-5°C, and add sodium nitrite dropwise Solution (34.5g sodium nitrite, 0.5mol, dissolved in 190g water), control the temperature at 10-20°C, control the dropping time for 4 hours, continue to react at this temperature for 1 hour after the dropping, and obtain diazotization The reaction solution.

[0042] (2) Sulfonyl chloride reaction

[0043] Add 250g of water and 765ml of hydrochloric acid (31%, 7.5mol) into a 5000ml three-necked bottle, stir in an ice-water bath, cool down to -5°C, and start feeding liquid sulfur dioxide, controlling the temperature at -3--1°C, when the When 64g of sulfur dioxide (1mol), the absorption of sulfur dioxide is completed, and the sulfonyl chloride reagent is obtained.

[0044] Add the diazotization reaction solution to the su...

Embodiment 2

[0048] (1) Diazotization reaction

[0049] Take 68.6g of p-aminobenzoic acid (0.5mol), 250g of water and 152.9ml of hydrochloric acid (31%, 1.5mol) into a 2000ml three-neck flask, stir in an ice-water bath, cool down to 0-5°C, and add sodium nitrite dropwise Solution (36.0g sodium nitrite, 0.52mol, dissolved in 190g water), control the temperature at 0-10°C, control the dropping time for 3 hours, continue to react at this temperature for 1 hour after the dropping, and obtain diazotization The reaction solution.

[0050] (2) Sulfonyl chloride reaction

[0051] Add 250g of water and 887ml of hydrochloric acid (31%, 8.7mol) into a 5000ml three-necked bottle, stir in an ice-water bath, cool down to -5°C, start to feed liquid sulfur dioxide, control the temperature at 0-5°C, when 112g of sulfur dioxide (1.75mol), the absorption of sulfur dioxide is complete, and the sulfonyl chloride reagent is obtained.

[0052] Add the diazotization reaction solution to the sulfonyl chloride rea...

Embodiment 3

[0056] (1) Diazotization reaction

[0057] Take 68.6g of p-aminobenzoic acid (0.5mol), 250g of water and 203.9ml of hydrochloric acid (31%, 2mol) into a 2000ml three-necked flask, stir in an ice-water bath, cool down to -10--5°C, and add nitrous acid dropwise Sodium solution (38.0g sodium nitrite, 0.55mol, dissolved in 190g water), control the temperature at 0-10°C, control the dropping time for 5 hours, continue to react at this temperature for 1 hour after the dropping, and obtain diazo chemical reaction solution.

[0058] (2) Sulfonyl chloride reaction

[0059] Add 250g of water and 968ml of hydrochloric acid (31%, 9.5mol) into a 5000ml three-necked bottle, stir in an ice-water bath, cool down to -5°C, start to feed liquid sulfur dioxide, control the temperature at 5-10°C, when 160g of sulfur dioxide (2.5mol), the absorption of sulfur dioxide is completed, and the sulfonyl chloride reagent is obtained.

[0060] Add the diazotization reaction solution to the sulfonyl chlo...

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Abstract

The invention belongs to the technical field of organic chemical synthesis, in particular to an aqueous phase synthesis method of probenecid. First, p-aminobenzoic acid, hydrochloric acid, and sodium nitrite are reacted to obtain a diazotization reaction liquid; then, liquid sulfur dioxide is passed into dilute hydrochloric acid aqueous solution to obtain a sulfonyl chloride reagent; then, the above two reaction liquids undergo a sulfonyl chloride reaction to obtain p-Carboxylbenzenesulfonyl chloride; finally, p-carboxybenzenesulfonyl chloride reacts with dipropylamine and is acidified to obtain pure probenecid. The synthesis process adopts aqueous phase synthesis technology, which changes the reaction path, reduces the generation of by-products, and avoids the use of organic solvents and highly toxic reagents; the product yield is ideal (91%, based on p-aminobenzoic acid), and the purity is high (98%). The development of the new synthesis process is conducive to the scale-up implementation of industrialization.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and specifically relates to an aqueous phase synthesis method of probenecid, which uses p-aminobenzoic acid as a raw material and water as a reaction medium to prepare p-carboxylate through diazotization and sulfonyl chloride reactions. Benzenesulfonyl chloride, and then react with dipropylamine to obtain probenecid. Background technique [0002] Probenecid, chemical name: p-(dipropylsulfamic acid) benzoic acid, English name: Probenecid; 4-[(Dipropylamino)sulfonyl]benzoic acid, molecular formula: C 13 h 19 NO 4 S, molecular weight: 285.36, white crystalline powder. The melting point is 194-196°C. Soluble in acetone, slightly soluble in ethanol or chloroform, almost insoluble in water. Soluble in dilute sodium hydroxide solution, almost insoluble in dilute acid. Odorless, slightly bitter taste. It is an adjunct to anti-gout drugs and antibiotic therapy. [0003] At prese...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C311/16C07C303/38
Inventor 胡波冯维春赵景瑞岳涛游淇李培培王云超迟金龙
Owner CHEM TECH ACAD OF SHANDONG PROVINCE
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