Transamidation of Primary Amides

Written by Dr Will Watson on Monday, 09 April 2012. Posted in Process Chemistry News

Many primary amides are commercially available but the list of commercially available secondary amides is much smaller.

This paper describes the transamidation of primary amides with secondary amines.  There is no requirement for an expensive transition metal or even a rare earth based catalyst but rather hydroxylamine hydrochloride is used as catalyst.

transamidation

There are 20 examples listed with yields generally 71-91%.  The reaction tolerates phenolic, hydroxy, akene, and alkyne groups are all tolerated along with Boc groups.  One other advantage of this method is that it allows formamide to be used to formylate amines.

C.L. Allen,* B.N. Atkinson, and J.M.J. Williams, Angew. Chem. Int. Ed., 2012, 51, 1383-1386.

About the Author

Dr Will Watson

Dr Will Watson

Will Watson gained his PhD in Organic Chemistry from the University of Leeds in 1980. He joined the BP Research Centre at Sunbury-on-Thames and spent five and a half years working as a research chemist on a variety of topics including catalytic dewaxing, residue upgrading, synthesis of novel oxygenates for use as gasoline supplements, surfactants for use as gasoline detergent additives and non-linear optical compounds. In 1986 he joined Lancaster Synthesis and during the next 7 years he was responsible for laboratory scale production and process research and development to support Lancaster’s catalogue, semi-bulk and custom synthesis businesses. In 1993 he was appointed to the position of Technical Director, responsible for all Production (Laboratory and Pilot Plant scale), Process Research and Development, Engineering and Quality Control. He helped set up and run the Lancaster Laboratories near Chennai, India and had technical responsibility for the former PCR laboratories at Gainesville, Florida. He joined Scientific Update as Technical Director in May 2000. He is also involved in an advisory capacity in setting up conferences and in the running of the events. He is active in the consultancy side of the business and sits on the Scientific Advisory Boards of various companies.

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