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Synlett 2014; 25(16): 2365-2369
DOI: 10.1055/s-0034-1378580
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of α-Functionalized Amides by a Ritter Reaction in the Presence of NaHSO4/SiO2

Mamiko Hayakawa
a   Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, ­Tokyo 101-8308, Japan   URL: aoyama.tadashi@nihon-u.ac.jp
,
Tadashi Aoyama*
a   Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, ­Tokyo 101-8308, Japan   URL: aoyama.tadashi@nihon-u.ac.jp
,
Toshiya Kobayashi
a   Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, ­Tokyo 101-8308, Japan   URL: aoyama.tadashi@nihon-u.ac.jp
,
Toshio Takido
a   Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, ­Tokyo 101-8308, Japan   URL: aoyama.tadashi@nihon-u.ac.jp
,
Mitsuo Kodomari
b   The Institute of Natural Science, College of humanities and Science, Nihon University, Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan
› Author Affiliations
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Publication History

Received: 12 June 2014

Accepted after revision: 11 July 2014

Publication Date:
13 August 2014 (online)

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Abstract

A simple and efficient method has been developed for the synthesis of α-functionalized amide from alcohols and nitriles in the presence of silica gel supported sodium hydrogen sulfate ­(NaHSO4/SiO2). For example, benzhydrol was allowed to react with bromoacetonitrile in the presence of NaHSO4/SiO2 in 1,2-dichloroethane to yield N-(diphenylmethyl)-2-bromoacetamide.

Key words

solid acid - alcohols - nitriles - amides - Ritter reactions

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