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Process for preparing 5-acetamino-N,N'-bis (2,3-dihydroxypropyl)-2,4,6-tri-iodo isophthalamide

A technology of triiodoisophthalamide and acetamido, which is applied in the chemical field, can solve the problems of heavy workload of intermediate separation, refining and baking, easy side reactions between intermediates and products, and impact on product quality, so as to avoid side effects. Responsive, easy to recycle, can be applied mechanically, and the effect of improving product quality

Inactive Publication Date: 2006-01-18
XINCHANG GUOBANG CHEM IND
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  • Abstract
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  • Claims
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Problems solved by technology

[0011] Among them, method 1 and method 2 are relatively common industrial synthesis methods currently adopted, and the reaction steps are relatively long, and the separation, refining and baking of intermediates require a large workload; and high-temperature recovery of DMAC, DMF, acetic anhydride and other high-boiling points are required. Solvents, intermediates and products are prone to side reactions at high temperatures; and using acetic anhydride as an acylating agent is difficult to recycle
[0012] Method 3 avoids the use of acetic anhydride as an acylating agent, but the separation of the intermediate (labeled 5 in the synthetic route of Method 3) and the product requires the recovery of high boiling point solvents, and side reactions are also prone to affect product quality

Method used

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  • Process for preparing 5-acetamino-N,N'-bis (2,3-dihydroxypropyl)-2,4,6-tri-iodo isophthalamide
  • Process for preparing 5-acetamino-N,N'-bis (2,3-dihydroxypropyl)-2,4,6-tri-iodo isophthalamide
  • Process for preparing 5-acetamino-N,N'-bis (2,3-dihydroxypropyl)-2,4,6-tri-iodo isophthalamide

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Embodiment 1

[0029] The preparation method of embodiment 1,5-acetylamino-N, N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide, with 5-nitroisophthalic acid As the main starting material, proceed as follows:

[0030] 1) Reduction: Add 120g of reduced iron powder, 38g of sodium chloride and 900ml of deionized water into a 1000mL three-necked bottle. Heat to 90°C and slowly add 42ml of concentrated hydrochloric acid, and heat to reflux for 30 minutes. Stop heating, slowly add 90g of 5-nitroisophthalic acid, heat and reflux for 6 hours after the addition, after the reaction is completed, cool to 65-70°C, adjust the pH value to 10-11 with 35% aqueous sodium hydroxide solution, and Filter iron sludge. The filtrate was adjusted to pH 4-4.5 with concentrated hydrochloric acid, and solids were precipitated, cooled to 5°C, filtered, and dried to obtain 75 g of compound (2), with a molar yield of 97.13%, HPLC: 98%.

[0031] 2), iodination: add 78.4g of compound (2) and 1600ml of deionized wa...

Embodiment 2

[0035] The preparation method of embodiment 2, 5-acetylamino-N, N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide differs from Example 1 in that , In step 3), 250ml of dioxane was used to replace 250mL of tetrahydrofuran to obtain 84.2g of product with a yield of 55.95%, HPLC: 97.8%.

Embodiment 3

[0036] Embodiment 3, the preparation method of 5-acetylamino-N, N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide: the difference from Example 1 is , In step 3), 300ml of cyclohexane was used to replace 250mL of tetrahydrofuran to obtain 76g of product with a yield of 50.51%, HPLC: 96.7%.

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Abstract

The preparation process of 5-acetylamino-N, N'-bis(2, 3-dihydroxypropyl)-2, 4, 6-triiodo isophthalamide with 5-nitro metaphthalic acid as initial material includes the following steps: the first reduction and iodation; dissolving 5-amino-2, 4, 6-triiodo isophthalic acid generated in the iodation step in solvent and adding thionyl chloride for reflux reaction of 1-18 hr; adding glacial acetic acid to reaction at 5-80 deg.c and washing; adding acid-binding agent, aminoglycerin and dimethyl methanamide to the washed organic layer to react at -10 deg.c to +50 deg.c; and filteing and cleaning after reaction. The preparation process of the present invention is simple, short, convenient in operation and high in yield.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to a preparation method of 5-acetylamino-N, N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide. Background technique [0002] Nonionic contrast agents are widely used in clinical diagnosis due to their low osmotic pressure, water solubility, and few side effects. 5-Acetamido-N, N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide is an intermediate of non-ionic contrast agents such as iohexol and iodixanol , English name: 5-acetamido-N, N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide, molecular formula: C 16 h 20 I 3 N 3 o 7 , the structural formula is as follows: [0003] [0004] 5-acetylamino-N, the synthetic method of N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide (I) mainly contains following three kinds at present: [0005] Method 1: Starting from 5-nitroisophthalic acid, undergo 5 steps of methyl esterification, transesterification, reduction, iodin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/32C07C231/14C07C231/02
Inventor 张卫东单国洋倪先锋竺亚庆
Owner XINCHANG GUOBANG CHEM IND
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