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Continuous Production Of The Diazomethane Precursor N-Methyl-N-nitroso-p-toluenesulfonamide: Batch Optimization And Transfer Into A Microreactor Setup

Michael Struempel, B. Ondruschka, A. Stark
Published 2009 · Chemistry

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The goal of this study was to develop a continuous multistep synthesis for the preparation of N-methyl-N-nitroso-p-toluenesulfonamide (3, MNTS, Diazald) starting from p-toluenesulfonyl chloride (1), making use of microreaction technology (MRT). MNTS is an important precursor for diazomethane, a highly reactive and selective reagent for the production of pharmaceuticals and fine chemicals. Due to the properties of the successive reaction steps (exothermic reactions, use of toxic and highly reactive reagents), it was envisaged that MRT could provide advantages when compared to its batch-wise preparation. The research strategy included preliminary batch investigations, in which the effects of the solvent system, feed concentration, relative molar ratio, temperature, and residence time were established. Starting from these results, the reactions were translated into the MRT setup. As a result, the amidation of 1 to N-methyl-p-toluenesulfonamide (2) as the first reaction step is performed continuously in >90% ...

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