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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
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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.
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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%.
[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%.
[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...
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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] ...
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