Improved preparation process of 5- amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzene dicarboxamide

A technology of phthalamide and dihydroxypropyl, which is applied to the preparation of carboxylic acid amides, the preparation of organic compounds, chemical instruments and methods, etc., which can solve the problem of low yield of the preparation method, difficult control of the production process, and danger to operators and other problems to achieve the effect of good reaction selectivity, high production cost and high safety

Active Publication Date: 2012-10-03
浙江海昌药业股份有限公司
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  • Abstract
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  • Application Information

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Problems solved by technology

Iodine monochloride is a toxic, harmful and highly corrosive product, which has strict requirements on packaging, transportation, and use. Improper use will cause danger to operators; iodine monochloride is prone to various side reactions during the reaction process, and the production process is not easy. control, the yield of the original preparation method is not high, and the production cost is very high

Method used

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  • Improved preparation process of 5- amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzene dicarboxamide

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Experimental program
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Effect test

Embodiment 1

[0022] The total amount of 5-amino-N, N'-bis(2,3-dihydroxypropyl)-1,3-benzenedicarboxamide aqueous solution obtained in the reaction was added to 340 grams of potassium iodide, 50 grams of sodium hydroxide, and 120 grams of trichloro Isocyanuric acid (TCCA), stirred and reacted at 0°C for 10 minutes, adjusted the pH of the solution to 5-7 with 25% sodium hydroxide, precipitated a solid, filtered to obtain 249 g of the product, melting point 176-178°C, yield 63.1%.

Embodiment 2

[0024] The total amount of 5-amino-N, N'-bis(2,3-dihydroxypropyl)-1,3-benzenedicarboxamide aqueous solution obtained in the reaction was added to 170 grams of potassium iodide, 50 grams of sodium hydroxide, and 40 grams of trichloro Isocyanuric acid (TCCA), stirred and reacted at 25°C for 100 minutes, adjusted the pH of the solution to 5-7 with 25% sodium hydroxide, precipitated a solid, and filtered to obtain 302 g of the product, with a melting point of 176-178°C and a yield of 76.5%.

Embodiment 3

[0026] The total amount of 5-amino-N, N'-bis(2,3-dihydroxypropyl)-1,3-benzenedicarboxamide aqueous solution obtained in the reaction was added to 250 grams of potassium iodide, 50 grams of sodium hydroxide, and 100 grams of trichloro Isocyanuric acid (TCCA), stirred and reacted at 0°C for 60 minutes, adjusted the pH of the solution to 5-7 with 25% sodium hydroxide, precipitated a solid, and filtered to obtain 319 g of the product, with a melting point of 176-178°C and a yield of 80.8%.

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Abstract

The invention discloses an improved preparation process of 5- amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzene dicarboxamide. The improved preparation process is characterized in that potassium iodide is taken as propiodal of 5- amino-N,N'-bis(2,3-dihydroxypropyl)-1,3-benzene dicarboxamide, and trichloroisocyanuric acid is taken as an oxidant thereof, so that the 5- amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzene dicarboxamide is obtained by iodination reaction. Further, the 5- amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzene dicarboxamide is a key intermediate for a non-ionic x-ray contrast medium such as iohexol, ioversol and iodixanol. The improved preparation process requires mild reaction conditions, and is convenient to operate, free of toxicity or pollution, high in iodine utilization rate and good in reaction selectivity; and production cost is lowered remarkably.

Description

technical field [0001] An improved method for preparing 5-amino-N, N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide, characterized in that 5- Amino-N, N'-bis(2,3-dihydroxypropyl)-1,3-benzenedicarboxamide is prepared by iodination reaction with potassium iodide as iodine source and trichloroisocyanuric acid as oxidant. Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide. 5-Amino-N, N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide is an important pharmaceutical intermediate, mainly used In the preparation of non-ionic x-ray contrast agents iohexol, ioversol and iodixanol. Background technique [0002] With the development of modern medicine and the application of more and more precision instruments, equipment and advanced technology, diagnostic medicine has also been developed rapidly. Among them, the development of iodine contrast agent has gone through three stages so far: [0003] In the first stage, from inorga...

Claims

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Application Information

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IPC IPC(8): C07C237/46C07C231/12
Inventor 张怀义刘颖平许志杰
Owner 浙江海昌药业股份有限公司
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