ChemicalBook CAS DataBase List Amiodarone

Amiodarone synthesis

5synthesis methods

Product Name:Amiodarone
CAS Number:1951-25-3
Molecular formula:C25H29I2NO3
Molecular Weight:645.31

Amiodarone, 2-butyl-3-benzofuranyl-4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl ketone (18.1.21), is synthesized in the following manner. Benzofuran is acylated by butyric acid anhydride in the presence of phosphorous acid, forming 2-butyroylbenzfuran (18.1.16). Reduction of the carbonyl group in a Wolff–Kizhner reaction using hydrazine hydrate gives 2-butylbenzofurane (18.1.17). This is acylated with 4-methoxybenzoic acid chloride, giving 2-butyl-3-(4-methoxybenzoyl)benzofuran (18.1.18), which undergoes demethylation by pyridine hydrochloride, forming 2-butyl-3-(4-hydroxy-benzoyl)-benzofuran (18.1.19). The resulting product is iodized in the presence of potassium iodide, forming 2-butyl-3-benzofuranyl-4-(2-hydroxy-3,5-diiodophenyl) ketone (18.1.20), which is reacted further with 2-diethylaminoethylchoride, giving desired amiodarone (18.1.21) .

100-06-1 Synthesis

100-06-1
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1951-25-3
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Yield:-

Steps:

Multi-step reaction with 5 steps
1: sodium hydride / mineral oil; tetrahydrofuran / Reflux
2: N-Bromosuccinimide; aluminum (III) chloride / nitromethane / 6 h / 80 °C
3: boron tribromide / dichloromethane
4: sodium hydroxide; iodine / methanol / 3 h / 0 - 20 °C
5: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 12 h / 20 °C

References:

Huang, Wenbo;Xu, Jing;Liu, Changhui;Chen, Zhiyan;Gu, Yanlong [Journal of Organic Chemistry,2019,vol. 84,# 5,p. 2941 - 2950]

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869-24-9 Synthesis