Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of iopromide

A technology of iopromide and hydroxypropylcarbamoyl, which is applied in the field of preparation of iopromide, can solve the problems of poor atom economy and increased cost of protecting groups, and achieve the effect of reducing production cost and improving atom economy

Active Publication Date: 2019-07-19
TAIZHOU UNIV
View PDF5 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this synthetic route, methoxyacetyl chloride is used for protection. Although the reaction steps are reduced, the cost of the protecting group is increased and the atom economy is poor.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of iopromide
  • Preparation method of iopromide
  • Preparation method of iopromide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] (S1) Preparation of 3-amino-5-chloroformylbenzoic acid methyl ester (formula III)

[0045] Add 10 g of 5-aminoisophthalic acid monomethyl ester (Formula II) and 20 ml of thionyl chloride into the reaction flask, and reflux for 4 hours. Distilled to dryness under reduced pressure to obtain 11.6 g of solid. The yield was 97.8%.

[0046] (S2) Preparation of 3-chloroformyl 5-[(methoxyacetyl)amino)]-benzoic acid methyl ester (formula IV)

[0047] Add 10 g of the compound of formula III, 100 ml of dioxane, and 7.1 g of methoxyacetyl chloride into the reaction flask, and stir the reaction for 6 h at room temperature. TLC detects that the reaction is complete. The solvent is evaporated under reduced pressure, and the next reaction is carried out directly.

[0048] (S3) Preparation of 3-[(2,3-dihydroxypropylcarbamoyl)-5-[(methoxyacetyl)amino]-benzoic acid methyl ester (Formula V)

[0049] In the reaction flask, add the reactants of the previous step, 5.1g of 3-aminopropanedio...

Embodiment 2

[0055] (S1) Preparation of 3-amino-5-chloroformylbenzoic acid methyl ester (formula III)

[0056] Add 10 g of 5-aminoisophthalic acid monomethyl ester (formula II), 5 ml of thionyl chloride, and 50 ml of dichloromethane into the reaction flask, and reflux for 5 h. Distilled to dryness under reduced pressure to obtain 11.7 g of solid. The yield is 98.7%.

[0057] (S2) Preparation of 3-chloroformyl 5-[(methoxyacetyl)amino)]-benzoic acid methyl ester (formula IV)

[0058] Add 10 g of the compound of formula III, 30 ml of DMF, and 5.6 g of methoxyacetyl chloride into the reaction bottle, and stir the reaction for 6 hours at room temperature. TLC detects that the reaction is complete. The solvent is evaporated under reduced pressure, and the next reaction is carried out directly.

[0059] (S3) Preparation of 3-[(2,3-dihydroxypropylcarbamoyl)-5-[(methoxyacetyl)amino]-benzoic acid methyl ester (Formula V)

[0060] Into the reaction bottle, add the reactants of the previous step, 6...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of iopromide. The method comprises the following steps: (1) chloridizing 5-methylaminoisophthalic acid monomethyl ester as shown in a formula II and used as a raw material to obtain 3-amino-5-chloroformylbenzoate as shown in a formula III; (2) enabling reaction between the compoundas shown in the formula III and methoxyacetyl chloride to obtain 3-chloroformyl 5-[methoxyacetyl)amino)]-methyl benzoate as shown in a formula IV; (3) enabling reaction between the compound as shown in the formula IV and 3-aminopropanediol to obtain 3-[(2,3-dihydroxypropylaminoformyl)-5-[(methoxyacetyl)amino]-methyl benzoate as shown in a formula V; (4) enabling reaction between the compound as shown in the formula V and 3-methylamino propanediol to obtain N,N'-di(2,3-dihydroxyl)-5-[(methoxyacetyl)amino)]-N-methyl-1,3-phthalamide as shown in a formula VI; and (5) enabling reaction between thecompound as shown in the formula VI and NaICl2 to obtain the iopromide. The preparation method of the iopromide provided by the invention is low in production cost, high in reproducibility and high inyield.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of iopromide. Background technique [0002] Iopromide (Formula I), chemical name: N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(methoxyacetyl)amino)] -N-methyl-1,3-benzenedicarboxamide, a new type of second-generation non-ionic hypotonic X-ray contrast agent, developed by German Schering AG company, the trade name is Ultravist (Ultravist), It was officially introduced to the market in 1985. It has the advantages of low toxicity, stable properties, isotonicity, and good tolerance. It is widely used in blood vessels and body cavities. Commonly used in cerebral angiography, enhanced CT scan, digital subtraction angiography, urography and various body cavity angiography. [0003] The synthesis of iopromide has multiple synthetic methods at present, and U.S. Patent No. 4,364,921A has reported three synthetic methods: [0004] method one: [0005] ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C237/46C07C231/02C07C237/42C07C235/16C07C227/18C07C229/60
CPCC07C231/12C07C231/02C07C227/18C07C237/46C07C237/42C07C235/16C07C229/60
Inventor 陈钢俞永浩杨健国吴岩磊吴昊陈佳雁蔡露露
Owner TAIZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com