ChemicalBook CAS DataBase List Iodixanol

Iodixanol synthesis

9synthesis methods

Product Name:Iodixanol
CAS Number:92339-11-2
Molecular formula:C35H44I6N6O15
Molecular Weight:1550.18

Iodixanol, developed by Nycomed in Norway, is a new type of non-ionic X-ray contrast agent, the only one that is isotonic with plasma when applied intravascularly. Iodixanol can be synthesized by three-step reaction using N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide as raw material.

31127-80-7 Synthesis

5-(Acetamido)-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide

31127-80-7
229 suppliers
$24.00/5g

106-89-8 Synthesis

106-89-8
746 suppliers
$9.00/10g

66108-95-0 Synthesis

66108-95-0
392 suppliers
$28.00/1g

92339-11-2
241 suppliers
$201.00/500MG

Yield:92339-11-2 86.3% ，66108-95-0 7.5%

Reaction Conditions:

with hydrogenchloride;boric acid;potassium hydroxide in water; pH=10 - 11;Product distribution / selectivity;Industry scale;

Steps:

1

Compound A (1120.5 kg, 1.50 kmol) was dissolved in a solution of KOH (140.0 kg, 2.25 kmol) in water (1232.6 kg), the temperature was controlled to below 20°C, boric acid (64.9 kg, 1.05 kmol) was equally added in a batch manner, and hydrochloric acid (30.4 kg, 0.30 kmol) was added dropwise, followed by epichlorohydrin (83.3 kg, 0.90 kmol), which was added dropwise. The pH during the reaction is 10-11. The reaction was monitored and a sample was analyzed by HPLC. The reaction was quenched by adding water (1232.6 kg) and adjusting the pH to within the range 5-6 with 18% of hydrochloric acid when the content of Compound A was below 5%.The reaction mixture was then decolorized with active charcoal and filtered. The filtrate contained 86.3% of iodixanol, 7.5% of iohexol, 2.9% of compound A and 2.7% of O-alkylated by-products and other impurities by HPLC analysis.

References:

WO2011/63551,2011,A1 Location in patent:Page/Page column 15-16

28659-12-3 Synthesis