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Synthesis method of key intermediate of diatrizoic acid

A synthetic method and intermediate technology, applied in the field of drug synthesis, can solve the problems of increasing risk and increasing production cost, and achieve the effect of controlling production cost and reaction safety

Pending Publication Date: 2022-03-22
安康市农业科学研究院
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Problems solved by technology

[0009] Among them, KICl 2 It is composed of elemental iodine, potassium iodide, potassium iodate, H 2 O and hydrochloric acid are formulated according to a certain ratio. Although the use of chlorine gas is avoided in the whole process, elemental iodine and potassium iodate are used in it, which increases the production cost virtually. Combustible materials, such as sulfur, phosphorus or metal powder, can form explosive mixtures, which increases the danger in the production process

Method used

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  • Synthesis method of key intermediate of diatrizoic acid
  • Synthesis method of key intermediate of diatrizoic acid
  • Synthesis method of key intermediate of diatrizoic acid

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preparation example Construction

[0032] This exemplary embodiment provides a synthetic method of a key intermediate of diatrizoic acid, which is 3,5-diamino-2,4,6-triiodobenzoic acid, characterized in that the synthetic method comprises the following steps:

[0033] (1) Using 3,5-diaminobenzoic acid, sulfuric acid, potassium iodide and hydrogen peroxide as reactants, reacting in a solvent environment to obtain crude 3,5-diamino-2,4,6-triiodobenzoic acid;

[0034] (2) Ammonia the crude product of 3,5-diamino-2,4,6-triiodobenzoic acid to obtain ammonium salt;

[0035] (3) Acidifying the ammonium salt to obtain the intermediate 3,5-diamino-2,4,6-triiodobenzoic acid.

[0036] Its reaction formula is as follows:

[0037]

[0038] The synthesis method of the key intermediate of diatrizoic acid in the embodiment of the present disclosure provides a new method for synthesizing the key intermediate of diatrizoic acid, which can effectively control the production cost and avoid the use of environmentally unfriendly...

Embodiment 1

[0041] Add 3,5-diaminobenzoic acid (50.0g) and purified water (2100ml) into a 5L jacketed bottle (R1), add sulfuric acid (50.0g) dropwise to the above system, add KI (180.0g) Add to R1, control the temperature at 30°C, add 30% H 2 o 2 (119.2g) was added dropwise to R1, after the dropwise addition was completed, the reaction temperature was adjusted to 55°C, and the reaction was carried out at this temperature for 3h. After the reaction is completed, adjust the temperature of the system to 20-25 ° C, and drop 10% sulfurous acid aqueous solution into the system until it is non-oxidizing (KI-I 2 test paper), stirred for 30min. Filter, transfer the crude product to a 2L jacketed bottle (R2), add saturated ammonium chloride aqueous solution (850g) to R2, adjust the pH to 9 with concentrated ammonia water, adjust the system temperature to 20°C, and stir at this temperature 3h, filtered to obtain light brown ammonium salt. Transfer the above ammonium salt to a 2L jacketed bottle ...

Embodiment 2

[0045] Add 3,5-diaminobenzoic acid (50.0g) and purified water (2000ml) into a 5L jacketed bottle (R1), add sulfuric acid (49.5g) dropwise to the above system, add KI (169.1g) Add to R1, control the temperature at 20°C, add 30% H 2 o 2 (115.5g) was added dropwise to R1, after the dropwise addition, the reaction temperature was adjusted to 50°C and reacted at this temperature for 1h. After the reaction is completed, adjust the temperature of the system to 20-25 ° C, and drop 10% sulfurous acid aqueous solution into the system until it is non-oxidizing (KI-I 2test paper), stirred for 30min, filtered, transferred the crude product to a 2L jacketed bottle (R2), added saturated aqueous ammonium chloride solution (750g) to R2, adjusted the pH to 8 with concentrated ammonia water, and adjusted the system temperature to 20°C , Stir at this temperature for 3h, filter the light brown ammonium salt. Transfer the above ammonium salt to a 2L jacketed bottle (R3), add purified water (900m...

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Abstract

The embodiment of the invention relates to a synthesis method of a key intermediate of diatrizoic acid, the intermediate is 3, 5-diamino-2, 4, 6-triiodobenzoic acid, and the synthesis method is characterized by comprising the following steps: taking 3, 5-diaminobenzoic acid, sulfuric acid, potassium iodide and hydrogen peroxide as reactants, and reacting in a solvent environment to prepare the 3, 5-diamino-2, 4, 6-triiodobenzoic acid. A 2, 6-triiodobenzoic acid crude product is obtained; then, the 3, 5-diamino-2, 4, 6-triiodobenzoic acid crude product is subjected to ammoniation, and ammonium salt is obtained; and acidifying the ammonium salt to obtain the intermediate 3, 5-diamino-2, 4, 6-triiodobenzoic acid. In the embodiment, a novel method for synthesizing the key intermediate of the diatrizoic acid is provided, the production cost can be effectively controlled, toxic chlorine unfriendly to the environment is prevented from being used, meanwhile, a dangerous reagent potassium iodate is prevented from being used, the reaction is safer, and the method is more suitable for industrial production.

Description

technical field [0001] The embodiment of the present disclosure relates to the technical field of drug synthesis, in particular to a method for synthesizing a key intermediate of diatrizoic acid. Background technique [0002] Diatrizoic acid, whose chemical name is 3,5-diacetamido-2,4,6-triiodobenzoic acid, is a positive contrast agent for X-ray diagnosis and is now included in the "Chinese Pharmacopoeia". It is generally formulated as diatrizoate meglumine, diatrizoate sodium or compound diatrizoate meglumine injection before application. Suitable for cardiovascular, aortic, various veins, excretory or retrograde urography, etc. The chemical structural formula of the key intermediate 3,5-diamino-2,4,6-triiodobenzoic acid of synthetic diatrizoic acid is shown in formula I: [0003] [0004] The synthetic route of industrial production is mainly as follows: [0005] [0006] 3,5-diaminobenzoic acid generates 3,5-diamino-2,4,6-triiodobenzoic acid under the action of i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/60C07C227/18C07C227/16C07C227/40
CPCC07C227/18C07C227/16C07C227/40C07C229/60
Inventor 徐聪周高新
Owner 安康市农业科学研究院
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