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首页> 外文期刊>Journal of Oleo Science >Amide Synthesis from Esters with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst
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Amide Synthesis from Esters with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst

机译：在无溶剂条件下使用分子碘作为催化剂由具有腈的酯合成酰胺

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摘要

The reaction of esters with nitriles, using iodine as a catalyst under solvent-free conditions, was investigated. For example, 1-phenylethyl acetate reacted with benzonitrile in the presence of iodine to afford the amide, N-(1-phenylethyl)benzamide. Addition of water was effective in promoting amidation. The most suitable conditions were investigated, and determined as follows: temperature = 80℃, molar ratio of nitrile:alcohol:iodine:water = 1:3:0.2:1.0, and reaction time = 18 h. The amidation reactivity depended on the stability of the cationic intermediate formed from the ester. Only the reaction of 2-phenylpropan-2-yl acetate with benzonitrile gave no amide compound; rather, the cyclic compound, 1,1,3-trimethyl-3-phenyl-2,3-dihydro-1H-indene was obtained in 90% yield. The reaction of (-)-bornyl acetate with benzonitrile produced the racemic amide compound, (±)-exo-N-isobornylbenzamide, in 82% yield.
机译：在无溶剂条件下，使用碘作为催化剂，研究了酯类与腈的反应。例如，乙酸1-苯乙基酯在碘的存在下与苄腈反应，得到酰胺N-（1-苯乙基）苯甲酰胺。加水可有效促进酰胺化。研究了最合适的条件，并确定如下：温度= 80℃，腈：醇：碘：水的摩尔比= 1：3：0.2：1.0，反应时间= 18 h。酰胺化反应活性取决于由酯形成的阳离子中间体的稳定性。仅乙酸2-苯基丙-2-基酯与苄腈的反应不产生酰胺化合物。相反，以90％的产率获得了环状化合物1,1,3-三甲基-3-苯基-2,3-二氢-1H-茚。 （-）乙酸乙酸烯丙酯与苄腈的反应产生了外消旋酰胺化合物，（±）-exo-N-异冰片基苯甲酰胺，收率为82％。

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  • 来源
    《Journal of Oleo Science》 |2012年第7期|p.393-399|共7页
  • 作者

    Yohko Hanzawa; Yoshio Kasashima; Kazuki Tomono; Takashi Mino; Masami Sakamoto; Tsutomu Fujita;

  • 作者单位

    Education Center, Faculty of Engineering, Chiba Institute of Technology (Shibazono 2-1-1, Narashino-shi, Chiba 275-0023, JAPAN);

    Education Center, Faculty of Engineering, Chiba Institute of Technology (Shibazono 2-1-1, Narashino-shi, Chiba 275-0023, JAPAN);

    Graduate School of Engineering, Chiba University (Yayoi-cho 1-33, Inage-ku, Chiba-shi, Chiba 263-8522, JAPAN);

    Graduate School of Engineering, Chiba University (Yayoi-cho 1-33, Inage-ku, Chiba-shi, Chiba 263-8522, JAPAN);

    Graduate School of Engineering, Chiba University (Yayoi-cho 1-33, Inage-ku, Chiba-shi, Chiba 263-8522, JAPAN);

    Graduate School of Engineering, Chiba University (Yayoi-cho 1-33, Inage-ku, Chiba-shi, Chiba 263-8522, JAPAN);

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类
  • 关键词

    iodine; solvent-free; ritter reaction; borneol;

    机译：碘;无溶剂itter反应冰片;

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