【作者】 杜梦；

【导师】 廖道华；

【作者基本信息】 华东理工大学 ， 制药工程与技术， 2011， 硕士

【摘要】 甲氧咪草烟是美国氰胺公司开发的咪唑啉酮类大豆田用除草剂。本文以马来酸二乙酯和盐酸羟氨为原料经过加成、脱水得到氨基马来酸二乙酯；同时以丙烯醛和甲醇经过加成再与甲醛缩合生成甲氧甲基丙烯醛,后者与氨基马来酸二乙酯反应得到重要中间体5-甲氧甲基-2,3-吡啶羧酸二乙酯,该中间体经过水解、酸化、脱水后得到5-甲氧甲基-2,3-吡啶二酸酐。以3-甲基-2-丁酮为原料与氯化铵和氰化钠经过Streker反应得到2-氨基2,3-二甲基丁腈,最后该中间体与5-甲氧甲基-2,3-吡啶二酸酐经加成、环合脱水、酸化得到目标产物甲氧咪草烟。对反应机理和主要影响因素如反应温度、反应时间、投料比等进行了探讨,确定了最佳的生产工艺条件。对重要中间体和产物结构用MS、1HNMR等进行了表征。更多还原

【Abstract】 Imazamox is a kind of Imidazolinone herbicides utilised in soybean field, which is developed and manufactured in American Cyanamid Company. In this paper, 1-amino-1,2-ethylenedicarboxylic acid esters was obtained from the reactants of diethyl maleate and hydroxylamine hydrochloride via addition and dehydration. The above product was reacted with methoxymethacrolein to produce 5-(methoxymethyl)-2,3-pyridinedicarboxylate; Methoxymethacrolein was synthesized from acrolein, methanol and formaldehyde. The intermediate 5-(methoxymethyl)-2,3-pyridine dicarboxylate further formed 5-(methoxymethyl)-2,3-pyridine dicarboxylic acid anhydride after hydrolysis, acidification and hydration reactions. Streker reaction was carried out in order to obtain another intermediate of 2-amino-2,3-dimethylbutyronitrile using 3-methylbutanone, ammonia chloride and sodium cyanide as the materials. Finally, Imazamox was synthesized by 2-amino-2,3-dimethylbutyronitrile and 5-(methoxymethyl)-2.3-pyridine dicarboxylic acid anhydride after addition, cyclodehydration, and acidification. The main mechanisms and influencing factors such as reaction temperature, reaction time, and the ratios of reactants are discussed here, in order to determine the optimum conditions for this total synthesis. The target product and some of the important intermediates were characterized by MS and’H NMR.更多还原