Amide Synthesis from Esters with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst
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- Hanzawa Yohko
- Education Center, Faculty of Engineering, Chiba Institute of Technology
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- Kasashima Yoshio
- Education Center, Faculty of Engineering, Chiba Institute of Technology
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- Tomono Kazuki
- Graduate School of Engineering, Chiba University
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- Mino Takashi
- Graduate School of Engineering, Chiba University
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- Sakamoto Masami
- Graduate School of Engineering, Chiba University
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- Fujita Tsutomu
- Graduate School of Engineering, Chiba University
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抄録
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°C, 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.
収録刊行物
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- Journal of Oleo Science
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Journal of Oleo Science 61 (7), 393-399, 2012
公益社団法人 日本油化学会
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詳細情報 詳細情報について
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- CRID
- 1390282679069685632
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- NII論文ID
- 130004719678
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- NII書誌ID
- AA11503337
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- COI
- 1:STN:280:DC%2BC38jpsFOltQ%3D%3D
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- ISSN
- 13473352
- 13458957
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- NDL書誌ID
- 023750464
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- PubMed
- 22790170
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可