Preparation of highly pure N-Formyl Benzotriazoles

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Chemical
Chemical

University: University of Glasgow

Sector(s): Chemical

About Opportunity:

Formylation is an integral part of organic, medicinal and biological chemistry both in industrial and academic set-ups.

Current formylating procedures suffer a number of disadvantages:

  • formic halides and formic anhydrides, tend to suffer from stability problems and are easily degraded upon storage. 
  • cyanomethyl formate is a very useful reagent, although it is difficult to prepare.
  • isopropenyl formate is a very fast and efficient reagent, but its synthesis requires a multi-step sequence. 
  • coupling agents have also been used in conjunction with formic acid to achieve N- and O-formylation, however, the removal of the side products derived from the coupling agents is often labour intensive.

N-formyl benzotriazole is a stable and convenient reagent to achieve quick and efficient N- and O- formylation of alcohols, amines and even amides in mild and selective manner.  The main challenge is the synthesis of N-formyl benzotriazole and its purification from the amount of urea by products.

Our patent protected synthesis of N-formyl benzotriazoles offers a product with much greater yield and higher purity compared to any previously known syntheses. The N-formyl benzotriazole is obtained by reacting a benzotriazole compound with a formyl anhydride.

Key Benefits:

  • Our new method of the synthesis of the N-formyl benzotriazole family of compound overcomes all of the following issues:
  • greater yield and purity compared to previously known syntheses.
  • •uses low molecular weight reagents that are readily produced from commercially available and cheap starting materials.
  • faster compared to known procedures.
  • avoids the need for carbodiimide coupling reagents, and thereby avoid the problems associated with the removal of carbodiimide-derived urea by-products.
  • suitable for large-scale production of N-formyl benzotriazoles on a multi gram scale without loss of yield or purity.

Applications:

  • N-formyl benzotriazole is a stable and convenient reagent to achieve quick and efficient N- and O- formylation of alcohols, amines and even amides in mild and selective manner.

IP Status:

A patent for this synthetic procedure was filed on 21 December 2010.

This technology is available as an Easy Access IP deal, available to companies and individuals to license for FREE.

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