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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 15, 1985 - Issue 14
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Original Articles

Facile Conversion of Primary Thioamides into Nitriles with Benzyl Chloride Under Phase Transfer Conditions

Yoshio Funakoshi Department of Industrial Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo, 101, Japan
,
Toshio Takido Department of Industrial Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo, 101, Japan
&
Kunio Itabashi Department of Industrial Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo, 101, Japan
Pages 1299-1303 | Published online: 03 Jan 2007
 
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Abstract

In previous paper1, we have reported the utility of P(NEt2)3/THF for the synthesis of nitriles from amides or thioamides. Dehydration of amides and dehydrosulfurization of thioamides into nitriles are commonly accomplished by using reagents such as P2O5 2; PPh3/CCI4?Et3N3; PPh3/THF/(EtOCON)2 4; DMF/NaOEt/α-haloketone, ester, nitrile5; n-Bu2Sno/MeOH, (n-Bu3Sn)2O/benzene6; polyphosphate7. Amides, aldoximes reacted with dichlorocarbene8 or carbon disulfide9 under phase transfer conditions to give corresponding nitriles, but the yield of nitriles from thiomides was not so good8.

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