1° Amides can be converted to Nitriles with Thionyl Chloride

1^o Amides can be converted to nitriles by reaction by dehydration with thionyl chloride.

General reaction

Example 1:

Mechanism

1) Nucleophilic attach on thionyl chloride

2) Leaving group removal

3) Deprotonation

4) Leaving group removal

Contributors

Prof. Steven Farmer (Sonoma State University)