Paper
Synthesis of 5-(4-Fluorophenylsulfonyloxy)-2-acetamino-nitrobenzene as the Intermediate of Luxabendazole
Published 2008 · Zhang Li
Fine chemicals
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Abstract
5-(4-Fluorophenylsulfonyloxy)-2-acetaminonitrobenzene is one of the main raw materials of Luxabendazole as a new anthelmintic.Starting from 4-aminophenol,reacting with acetic anhydride under reflux for 3 h,adding 98% HNO3 dropwise under stirring for 1.5 h,and then adding 65% HNO3 dropwise slowly for 1.5 h(the temperature not exceeding 25 ℃),4-acetoxy-2-nitroacetanilide(Ⅰ) was prepared.Then Ⅰ and NaOH in mole ratio 1∶0.25 reacted in 95% ethanol under reflux for 1 h to afford 4-acetamino-3-nitrophenol(Ⅱ).Finally,5-(4-fluorophenylsulfonyloxy)-2-acetaminonitrobenzene(Ⅲ) was obtained by condensation of Ⅱand p-fluorobenzenesulfonyl chloride in mole ratio 1∶1.1 for 4 h at 25～30 ℃.The total yield of Ⅲ amounted to 65%.Structures of the products were confirmed by IR,HRMS and 1HNMR.The novelty of this procedure was confirmed in novelty search innovation report of science and technology offered by Jiangsu New Methods Consultation Center on 17th,November 2006(serial number 200632B2503543).
The study presents a novel method for preparing 5-(4-fluorophenylsulfonyloxy)-2-acetaminonitrobenzene, an intermediate in Luxabendazole, with a 65% yield and confirmed structure-based synthesis.
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