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Preparation technology of iopromide intermediate

A technology of iopromide and preparation process, applied in the field of drug synthesis, can solve problems such as inability and high yield, and achieve the effects of low cost, high yield and simple synthesis route

Inactive Publication Date: 2016-01-20
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the inventors repeated the experimental operation and found that they could not obtain a very small amount of the target product-compound 10a in a higher yield.

Method used

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  • Preparation technology of iopromide intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The synthesis of embodiment 1.5-nitroisophthalic acid dimethyl ester

[0034] In a 100mL round-bottomed flask equipped with a condenser, an electric stirrer and a thermometer, add 5.0g of 5-nitroisophthalic acid, add 33.3ml of methanol, and 2 Stir at room temperature, about 3min, the solid dissolves completely, the solution is colorless, clear and transparent, then slowly add 1.0ml of concentrated sulfuric acid under stirring, heat up and reflux, about 3h there is white solid precipitation, TLC traces the reaction, developing agent (CH 2 Cl 2 :CH 3 OH=10:1), cooled and crystallized, filtered, washed with a small amount of water, and the filter cake was dried to obtain dimethyl 5-nitroisophthalate, which was weighed and the yield was 98%. 1HNMR (CDCl 3 ) δ: 8.92-9.18 (m, 3H), 3.98 (s, 6H).

Embodiment 2

[0035] The synthesis of embodiment 2.5-nitroisophthalic acid monomethyl ester

[0036] Add 2.5g of dimethyl 5-nitroisophthalate and 38.5mL of methanol into a 250mL four-neck flask with a stirrer, condenser and thermometer, heat and stir to dissolve, then add 0.42g dropwise within 20min and dissolve with 5g of water Sodium hydroxide solution, heated and refluxed for 2h, TLC tracked the reaction until the raw material point disappeared, developing agent (petroleum ether: CH 2 Cl 2 =5:1); after taking a small amount of acid for acidification, use 5-nitroisophthalic acid and 5-nitroisophthalic acid monomethyl ester as a control, and see if there is any product formation and 5-nitroisophthalic acid on TLC. The appearance of phthalic acid, developing agent (CH 2 Cl 2 :CH 3 OH=5:1). After the reaction, methanol was distilled off, 26mL of water was added, filtered while hot, and the filtrate was acidified with concentrated hydrochloric acid to a pH value of 1, and crystals were p...

Embodiment 3

[0037] Example 3. Synthesis of 3-(2,3-dihydroxypropylcarbamoyl)-5-nitroisophthalic acid (compound 10a)

[0038] In a 50mL round-bottomed flask equipped with a condenser, an electric stirrer and a thermometer, add 400mg of 5-nitroisophthalic acid monomethyl ester, add 4ml of tert-butanol, stir at room temperature, the solid is not dissolved, add 194mg of 3-amino-1,2 -Propylene glycol and 598mg potassium tert-butoxide, the solid is dissolved, and the color of the solution changes from white to brown. Under an atmosphere of nitrogen, the temperature is raised to reflux, and the reaction is tracked by TLC until the raw material point disappears. The operation is as follows: take 1 drop of the solution, add 1 drop h 2 O, adjust the pH to 1 with concentrated HCl and spot the plate with the raw material (developing agent CH 3 OH:CH 2 Cl 2 : glacial acetic acid=2:1: glacial acetic acid), after the reaction, distill tert-butanol, add 2mlH 2 O, adjust the pH to 1 with concentrated H...

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Abstract

The invention provides an iopromide intermediate. A preparation technology of a compound 3-(2,3-dihydroxypropyl formamyl)-5-nitroisophthalic acid comprises the steps that monomethyl 5-nitroisophthalate is reacted with 3-amino propane-1,2-diol in alcohol solvent at appropriate heating temperature on the condition that strong alkali exists to obtain a product, wherein the reaction equation is shown in the specification. According to the preparation technology of the iopromide intermediate, the synthetic technology is good in selectivity, the synthetic route is simple, the product can be obtained through simple filtration, and the yield is high. Therefore, the technology has the advantages of being efficient, rapid and low in cost.

Description

Technical field [0001] The invention belongs to the field of drug synthesis, and specifically relates to the preparation process of non-ionic iodine contrast agent iopromide synthesis intermediate-3-(2,3-dihydroxypropylcarbamoyl)-5-nitroisophthalic acid compounds. . Background technique [0002] The rapid development of modern medical imaging technology has promoted the development process of my country's contrast agent market. Nowadays, it has developed from the initial stage of radiographic contrast agents to multiple fields such as computed tomography, ultrasound contrast agents, digital subtraction, magnetic resonance imaging, and arteriography. In recent years, the use of contrast preparations has become more and more widespread. In modern radiological diagnosis and treatment, contrast preparations are commonly used for disease examination and diagnosis. Therefore, it is imperative to improve the competitiveness of my country's production of contrast agents. The first...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/69C07C231/02
Inventor 赵长阔王先恒马家会杨福红
Owner ZUNYI MEDICAL UNIVERSITY
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