UC-781

N-[4-氯-3-(3-甲基丁-2-烯氧基)苯基]-2-甲基呋喃-3-硫代甲酰胺Chemical Name: N-[4-Chloro-3-(3-methyl-2-butenyloxy)phenyl]-2-methylfuran-3-carbothioamide
CAS No. 178870-32-1
项目整合开发状态: Phase I
项目研究机构: Cellegy (Proprietary), Uniroyal (Originator), University of Pittsburgh (Originator), Biosyn (Licensee)
合成路线:The diazonium salt prepared from 2-amino-5-nitrophenol (I) was subjected to Sandmeyer reaction in the presence of HCl and CuCl to afford the chlorophenol derivative (II).Subsequent alkylation of phenol (II) with prenyl bromide (III) produced ether (IV).Amine (V) was then obtained by reduction of the nitro group of (IV) employing iron powder in the presence of HCl.

合成路线:Chloroacetaldehyde (VII),prepared by acid hydrolysis of the dimethyl ketal (VI),was condensed with ethyl acetoacetate (VIII) to produce ethyl 2-methyl-3-furoate (IX).Basic hydrolysis of ester (IX),followed by chlorination of the resultant carboxylic acid (X) with SOCl2,gave acid chloride (XI).Then,condensation of amine (V) with acid chloride (XI) yielded amide (XII),which was finally converted to the title thioamide by treatment with Lawesson's reagent in hot toluene.