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Method for preparing 5-acetamido-2,4,6-triiodo-1,3-benzenedicarboxamides

A technology of phthalamide and acetamido, applied in the field of 5-acetamido-2, can solve problems such as environmental pollution, and achieve the effects of less environmental pollution, high yield and low production cost

Active Publication Date: 2008-06-04
ZHEJIANG HAIZHOU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is also an environmental pollution problem in this reaction route

Method used

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  • Method for preparing 5-acetamido-2,4,6-triiodo-1,3-benzenedicarboxamides
  • Method for preparing 5-acetamido-2,4,6-triiodo-1,3-benzenedicarboxamides
  • Method for preparing 5-acetamido-2,4,6-triiodo-1,3-benzenedicarboxamides

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Experimental program
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Effect test

Embodiment 1

[0023] In the 1000 milliliter reaction bottle, add 5-acetamido-2,4,60 grams (0.1 moles) of triiodoisophthalic acid, 8 grams (0.1 moles) of catalyst pyridine, 12.8 grams (0.04 moles) of solid phosgene, 100 ml of 1-butyl-3-methylimidazolium tetrafluoroborate, heated up to 100°C, stirred, and reacted for 4 hours. After the reaction, cooled to below room temperature, 20 ml of ammonia water (25%) was added dropwise while stirring, Raise the temperature to 60°C, stir for 3 hours, after the reaction is complete, cool to room temperature, filter, and discard the filtrate to obtain 48 grams of the product 5-acetamido-2,4,6-triiodo-1,3-benzenedicarboxamide, melting point > 300 °C, yield 80%. The filtrate obtained by filtration was extracted with dichloromethane, and the dichloromethane layer was taken to evaporate the solvent to obtain 1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid, which was used for recycling.

Embodiment 2

[0025] In the 1000 milliliter reaction bottle, add 5-acetamido-2,4,60 grams (0.1 moles) of triiodoisophthalic acid, 8 grams (0.1 moles) of catalyst pyridine, 12.8 grams (0.04 moles) of solid phosgene, 100 ml of 1-ethyl-3-methylimidazolium tetrafluoroborate was heated up to 100° C., stirred, and reacted for 4 hours. After the reaction was completed, it was cooled to below room temperature, and 20 ml of ammonia water (25%) was added dropwise while stirring. Raise the temperature to 60°C and stir for 3 hours. After the reaction is complete, cool to room temperature and filter to obtain 48 grams of the product 5-acetylamino-2,4,6-triiodo-1,3-benzenedicarboxamide with a melting point of >300°C. Yield 80%. Extract the filtrate obtained by filtration with dichloromethane, take the dichloromethane layer and evaporate the solvent to obtain 1-ethyl-3-methylimidazolium tetrafluoroborate ionic liquid, which is used for recycling.

Embodiment 3

[0027] In the 1000 milliliter reaction bottle, add 5-acetamido-2,4,60 grams (0.1 moles) of triiodoisophthalic acid, 16 grams (0.2 moles) of catalyst pyridine, 38.4 grams (0.12 moles) of solid phosgene, 100 ml of 1-butyl-3-methylimidazolium hexafluorophosphate, heated up to 100°C, stirred, and reacted for 4 hours. After the reaction, cooled to below room temperature, 50 ml of ammonia water (25%) was added dropwise with stirring, and heated Stir at 60°C for 3 hours, after the reaction is complete, cool to room temperature, filter, and discard the filtrate to obtain 50 grams of the product 5-acetylamino-2,4,6-triiodo-1,3-phthalamide, melting point > 300°C , yield 83%. Extract the filtrate obtained by filtration with dichloromethane, take the dichloromethane layer and evaporate the solvent to obtain 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid, and the ionic liquid is used for recycling.

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Abstract

The invention relates to a method for preparing 5-acetylamino-2, 4, 6-triiodide-1, 3-phthalic diamide. 5-acetylamino-2, 4, 6-triiodide isophthalic acid is adopted as raw material and ionic liquid is used as a reaction medium, which firstly are acyl chloridized with triphosgene under the function of catalyst and amidated after the acyl chloridization reaction, thus obtaining the target product after separation and purification. The catalyst is organic amine compound and the ionic liquid is selected from imidazole salt, pyridinium salt, quaternary ammonium salt or quaternary phosphor salt. The method of the invention is suitable for carrying out scale industrial production with relatively small environmental pollution, high yield and low production cost.

Description

(1) Technical field [0001] The invention relates to a preparation method of 5-acetylamino-2,4,6-triiodo-1,3-benzenedicarboxamide. (2) Background technology [0002] 5-Acetamido-2,4,6-triiodo-1,3-benzenedicarboxamide (formula I) is the key intermediate of the non-ionic monomer contrast agent iohexol, and is also the key intermediate for the synthesis of non-ionic dimer contrast agent It is an important intermediate of the agent iodixanol and has broad application prospects. [0003] [0004] At present, the synthetic routes of iohexol and iodixanol intermediates generally contain the following three types: [0005] 1. Using 5-nitroisophthalic acid as raw material, it is firstly esterified with methanol, then acylated with 1-amino-2,3-propanediol respectively, hydrogenated for reduction, iodized and then acylated with acetic anhydride. In this process route, due to the premature combination of 1-amino-2,3-propanediol into the molecule and the existence of multiple hydroxy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/46C07C231/02
Inventor 管宜河裴文郑金星陈昌略于小红
Owner ZHEJIANG HAIZHOU PHARMA CO LTD
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