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ChemicalBook CAS DataBase List Iohexol
66108-95-0

Iohexol synthesis

11synthesis methods
5-(Acetamido)-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide

31127-80-7

Epichlorohydrin

106-89-8

Iohexol

66108-95-0

Iodixanol

92339-11-2

N1,N3-bis(2,3-dihydroxypropyl)-5-(N-(2,3-dihydroxypropyl)acetamido)-2,4,6-triiodomethylbenzene dicarboxamide (Compound A, 1120.5 kg, 1.50 kmol) and 1-chloro-2,3-propylene oxide were synthesized as 5-(acetamido)-N,N'-bis(2,3-dihydroxypropyl)-5-(N-(2,3-dihydroxypropyl)acetamido)-2,4,6- Triiodo-m-toluene dicarboxamide and 5,5'-((2-hydroxypropyl-1,3-diyl)bis(acetylazanediyl))bis(N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-m-toluene dicarboxamide) in the following general steps: 1. dissolve compound A (1120.5 kg, 1.50 kmol) in a solution of water (1232.6 kg) containing KOH (140.0 kg, 2.25 kmol), controlling the temperature below 20 °C. 2. boric acid (64.9 kg, 1.05 kmol) and hydrochloric acid (30.4 kg, 0.30 kmol) were added in batches. 3. 1-chloro-2,3-epoxypropane (83.3 kg, 0.90 kmol) was added slowly and dropwise, keeping the pH of the reaction system between 10-11. 4. The progress of the reaction was monitored by HPLC during the reaction. 5. When the content of compound A was below 5%, the reaction was quenched by addition of water (1232.6 kg) and the pH was adjusted to 5-6 with 18% hydrochloric acid. 6. The reaction mixture was decolorized by activated carbon and filtered. 7. HPLC analysis showed that the filtrate contained 86.3% iodixanol, 7.5% iodohexanol, 2.9% compound A and 2.7% O-alkylation by-products and other impurities.

31127-80-7 Synthesis
5-(Acetamido)-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide

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

92339-11-2 Synthesis
Iodixanol

92339-11-2
274 suppliers
$190.00/

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

Reaction Conditions:

with hydrogenchloride;boric acid;potassium hydroxide in water; pH=10 - 11Product 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:

HOVIONE CHINA HOLDING LIMITED;HU, Zhiqi;ZHANG, Huoying WO2011/63551, 2011, A1 Location in patent:Page/Page column 15-16

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