4-氨基-5-[2-(4-氯苯氧甲基)苯并咪唑-1-亚甲基]-1,2,4-三唑-3-硫酮的核磁共振研究  

Study on Nuclear Magnetic Resonance of 4-Amino-5-[2-(4-chlorophenoxymethyl)benzimidazole-1-methylene]-1,2,4-triazole-3-thione

作　　者：李英俊[1] 刘丽军[1] 许永廷[1] 孙淑琴[1] 

机构地区：[1]辽宁师范大学化学化工学院,大连116029

出　　处：《分析化学》2011年第6期902-905,共4页Chinese Journal of Analytical Chemistry

基　　金：辽宁省自然科学基金(No.20102126);辽宁省教育厅高等学校科研基金(No.2008345)资助

摘　　要：在无水乙醇和KOH存在下,将2-(4-氯苯氧甲基)-1-苯并咪唑乙酰肼(1)与CS2反应,合成出了中间体酰肼二硫代甲酸钾盐。此中间体再与过量的水合肼反应,经环化得到一种新化合物4-氨基-5-[2-(4-氯苯氧甲基)苯并咪唑-1-亚甲基]-1,2,4-三唑-3-硫酮。采用元素分析、IR及NMR技术确定了新化合物的结构,并利用2D NMR技术对其两种异构体(硫酮和硫醇)的1H和13C NMR谱带进行了全归属,给出了相应的偶合常数J值以及异构体所占的比例。实验表明,新化合物在DMSO中存在硫酮和硫醇两种异构体的互变,并且硫酮占主导,含量为81.9%,而硫醇的含量仅为18.1%。A new compound,4-amino-5-[2-（4-chlorophenoxymethyl）benzimidazole-1-methyl-ene]-1,2,4-triazole-3-thione（3）,was synthesized by the reaction of the potassium dithiocarbazinate（2） with excess hydrazine hydrate.The compound 2 was obtained by the reaction of the hydrazide（1） with carbon disulfide in the presence of absolute ethanol and potassium hydroxide.The structure of the new compound 3 was determined by elemental analysis,IR and NMR techniques.The 1H and 13C NMR signals of two isomers（thione and thiol） of the compound 3 were assigned completely using 2D NMR techniques,and the corresponding coupling constants and the tautomeric ratios of isomers were also given out.Experimental results show that the target compound 3 in dimethyl-sulfoxide（DMSO） exists in the tautomerism of the thione and thiol,and the ratio of the dominant thione was 81.9%,while the thiol was 18.1%.

关 键 词：1 2 4-三唑类衍生物 核磁共振波谱 结构解析 互变异构 

分 类 号：O626.23[理学—有机化学]