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5-氯-3-(2-噻吩甲酰)-1-甲酰胺-2-羟基吲哚钠盐的合成
引用本文:吴星华,岳宏飞.5-氯-3-(2-噻吩甲酰)-1-甲酰胺-2-羟基吲哚钠盐的合成[J].华西药学杂志,2001,16(1):8-10.
作者姓名:吴星华  岳宏飞
作者单位:四川抗菌素工业研究所化学制药一室,
摘    要:目的:合成具抗炎活性的5-氯-3(2-噻吩甲酰)-1-甲酰胺-2-羟基吲哚钠盐。方法:以对氯苯胺为起始原料,经四步反应制得关键中间体5-氯-2-羟基吲哚,收率75%,然后与三氯乙酰异腈酸酯和2-噻吩甲酰氯反应,最后经NaHCO3处理,制得标题化合物。结果:总有收率可达45%以上,标题化合物经红外光谱、核磁共振谱、质谱及元素分析确证了结构,结论:该实验方法条件温和,操作简单、收率高,适合大规模合成。

关 键 词:甲酰胺  羟基吲哚钠盐  合成  非甾体抗炎药
文章编号:1006-0103(2001)01-0008-03

SYNTHESIS OF SODIUM SALT OF 5-CHLORO-3-(2-THENOYL)-2-OXINDOLE-1-CARBOXYAMIDE
WU Xing-hua,YUE Hong-fei.SYNTHESIS OF SODIUM SALT OF 5-CHLORO-3-(2-THENOYL)-2-OXINDOLE-1-CARBOXYAMIDE[J].West China Journal of Pharmaceutical Sciences,2001,16(1):8-10.
Authors:WU Xing-hua  YUE Hong-fei
Abstract:OBJECTIVE:A facile synthesis of sodium salt of 5 chloro 3 (2 thenoyl) 2 oxindole 1 carboxyamide from common 4 chloroaniline is described.METHODS:The key intermediate 5 chloro 2 oxindole(4) is prepared successfully in 75% yield from 4 chloroaniline in four steps, and converted by reaction with trichloroacetyl isocyanate into the N trichloroacetyl 5 chloro 2 oxindole 1 carboxyamide,and followed hydrolysis, then 5 chloro 2 oxindole 1 carboxyamide(5) is obtained. Condensation of (5) with 2 thenoyl chloride gives 5 chloro 3 (2 thenoyl) 2 oxindole carboxyamide(6). The title compound is obtained by treating(6) with NaHCO 3.RESULTS:The title compound is prepared successfully over 45% yield. The structure is characterized by elementary analysis,IR,MS, 1H NMR,H H COSY, 13 C NMR ,DEPT and HMQC. CONCLUSION:The method is simple and applicable to large scale preparation
Keywords:chloro  3  (2  thenoyl)  2  oxindole  1  carboxyamide  5  chloro  2  oxindole  Cycloxyenase & 5  lipoxygenase  Enzyme inhibitor  Non  steroidal anti  inflammatory activity & non  steroid
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