ChemicalBook CAS DataBase List Levamisole

Levamisole synthesis

14synthesis methods

Product Name:Levamisole
CAS Number:14769-73-4
Molecular formula:C11H12N2S
Molecular Weight:204.29

Levamisole, 2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole (31.1.4), is synthesized in various ways. One of them begins with α-bromoacetophenone, the reaction of which with 2-imino-1,3-thiazolidine gives 3-phenacyl-2-imino-1,3-thiazolidine (31.1.1). Reacting this product with acetic anhydride gives 3-phenacyl-2-acetylimino-1,3- thiazolidine (31.1.2). The ketone group in the resulting compound is reduced to an alcohol using sodium borohydride, and the resulting hydroxyl group in (31.1.3) is replaced with chlorine using thionyl chloride. Heating the product in acetic anhydride, the imidazole cycle closes, forming the product (31.1.4).

A somewhat different approach was realized when using styrene oxide as the initial starting material. Reacting it with 2-imino-1,3-thiazolidine gives 3-(2-phenyl-2-hydroxyethyl)- 2-imino-1,3-thiazolidine (31.1.5), which is subsequently treated with thionyl chloride and then acetic anhydride to give the desired levamisole (31.1.4).
Finally, the following scheme of making the product has been proposed using the same styrene oxide. Styrene oxide is reacted with aziridine, forming 2-aziridion-1- phenylethanol-1 (31.1.6). Treating this with potassium isothiocyanate or thiourea gives 3- (2-phenyl-2-hydroxyethyl)-2-amino-1,3-thiazolidine (31.1.5), and subsequent treatment with thionyl chloride (such as described above) and then with acetic anhydride gives the desired levamisole (31.1.4).

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Yield:14769-73-4 85%

Reaction Conditions:

with thionyl chloride in dichloromethane at 20 - 30; for 2 h;

Steps:

2. In the reaction flask, add 30.0 g of compound (IV),150g dichloromethane,15.2g thionyl chloride, react at 20-30 for 2h,Remove the solvent under reduced pressure, add 100 g of ethanol to dissolve, cool to 0-8 °C for crystallization, filter,A nearly white solid was obtained, which was added to 180 g of water, and at room temperature,Add dropwise sodium hydroxide solution (4.6g sodium hydroxide dissolved in 15g water), stir for 1h,filter,20.1 g of near-white solid compound (V) was obtained with a yield of 85%;

References:

CN114315753,2022,A Location in patent:Paragraph 0053-0054; 0057

16595-80-5 Synthesis