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A kind of 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, increased cost of protecting groups and the like, and achieves the effects of reducing production cost and improving atom economy

Active Publication Date: 2022-01-21
TAIZHOU UNIV
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  • 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

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  • A kind of preparation method of iopromide
  • A kind of preparation method of iopromide
  • A kind of 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 was 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 flask. 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, 6.3g ...

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Abstract

The invention belongs to the technical field of chemical synthesis, and be specifically related to a preparation method of iopromide, said method comprising: (1) using 5-aminoisophthalic acid monomethyl ester shown in formula II as a raw material, preparing iopromide through chlorination 3-amino-5-chloroformyl benzoic acid methyl ester shown in formula III; (2) formula III compound reacts with methoxyacetyl chloride to prepare 3-chloroformyl 5-[(formyl chloride) shown in formula IV Oxyacetyl) amino)]-methyl benzoate; (3) formula IV compound and 3-aminopropanediol reaction make 3-[(2,3-dihydroxypropylcarbamoyl)-5 shown in formula V ‑[(Methoxyacetyl) amino]‑methyl benzoate; (4) reacting the compound of formula V with 3-methylaminopropanediol to prepare N,N′-bis(2,3-dihydroxy Propyl)-5-[(methoxyacetyl) amino)]-N-methyl-1,3-phthalamide; (5) formula VI compound and NaICl 2 The reaction produces iopromide. The preparation method of iopromide provided by the invention has low production cost, good reproducibility and high yield.

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

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Application Information

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Patent Type & Authority Patents(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
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