【结 构 式】 |
【分子编号】12948 【品名】1-(1-Benzothiophen-2-yl)-1-ethanone oxime 【CA登记号】 |
【 分 子 式 】C10H9NOS 【 分 子 量 】191.2536 【元素组成】C 62.8% H 4.74% N 7.32% O 8.37% S 16.77% |
合成路线1
该中间体在本合成路线中的序号:(II)The synthesis of zileuton involved conventional synthetic procedures starting with 2-acetylbenzo[b]thiophene. Treatment of a solution of 2-acetylbenzo[b]thiophene (I) in ethanol/pyridine (1:1) with hydroxylamine hydrochloride at room temperature provided the corresponding oxime (II). To the oxime (II) dissolved in ethanol was added borane:pyridine complex followed by the dropwise addition of 20% HCl in ethanol to provide the hydroxylamine (III), isolated by extraction after neutralization of the acidic mixture. The hydroxylamine (III) was converted to zileuton by either heating with trimethylsilylisocyanate in dioxane or by reacting with KOCN and aqueous HCl.
【1】 Summers, J.B. Jr.; Gunn, B.P.; Brooks, D.W. (Abbott Laboratories Inc.); Indole, benzofuran, benzothiophene containing lipoxygenease inhibiting compounds. EP 0279263; JP 1988264456; US 4873259 . |
【2】 Brooks, D.W.; Rubin, P.D.; Carter, G.W.; Dube, L.M.; Bell, R.L.; Zileuton. Drugs Fut 1993, 18, 7, 616. |