Web Release Date: October 8,
Identification of New Catalysts to Promote Imidazolide Couplings and Optimisation of Reaction Conditions Using Kinetic Modelling
and
Department of Chemical Research and Development, Pfizer Global Research and Development, Sandwich, Kent CT13 9NJ, United Kingdom, and Medway Sciences, University of Greenwich, Medway Campus, Chatham, Kent ME4 4TB, United Kingdom
Received for review June 23, 2004.
Abstract:
Three catalysts were used to promote an imidazolide coupling. These catalysts were 2-hydroxypyridine (HOPy), endo-N-hydroxy-5-norbornene-2,3-dicarboximide (HONB) (both reported for the first time to catalyse this type of reaction), and 1-hydroxybenzotriazole (HOBt). The thermal safety, cost, and catalytic effectiveness of these three catalysts are compared. In addition, kinetic modelling using the Dynochem software was used to optimise the HOBt- and HOPy-catalysed reactions. By use of this simulation method, the optimal reaction conditions, such as catalyst quantity, reaction time, and reaction temperature were predicted. Subsequent experiments confirmed that the predictions were accurate.
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