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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% ...



This paper is referenced by
10.1021/acs.oprd.0c00485
Scalable On-Demand Production of Purified Diazomethane Suitable for Sensitive Catalytic Reactions
Jillian W. Sheeran (2020)
10.1002/CEAT.201400723
Bromination of Aromatic Compounds using Bromine in a Microreactor
Qiulin Deng (2016)
10.1556/1846.2015.00046
One-Pot Synthesis of α-Haloketones Employing a Membrane-Based Semibatch Diazomethane Generator
S. Garbarino (2016)
10.1039/c5cs00902b
Taming hazardous chemistry by continuous flow technology.
M. Movsisyan (2016)
10.1002/anie.201409318
Continuous-flow technology—a tool for the safe manufacturing of active pharmaceutical ingredients.
Bernhard Gutmann (2015)
10.1002/ANGE.201409318
Kontinuierliche Durchflussverfahren: ein Werkzeug für die sichere Synthese von pharmazeutischen Wirkstoffen
Bernhard Gutmann (2015)
10.1002/chem.201500416
Rapid Generation and Safe Use of Carbenes Enabled by a Novel Flow Protocol with In-line IR spectroscopy.
Simon T. R. Mueller (2015)
10.1039/c4sc03072a
Flow chemistry as a discovery tool to access sp2–sp3 cross-coupling reactions via diazo compounds† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc03072a Click here for additional data file.
D. Tran (2015)
10.1002/chem.201404348
Taming hazardous chemistry in flow: the continuous processing of diazo and diazonium compounds.
Benjamin J. Deadman (2015)
10.1021/OP400179F
Improved Continuous Flow Processing: Benzimidazole Ring Formation via Catalytic Hydrogenation of an Aromatic Nitro Compound
J. Chen (2014)
10.1021/jo402849z
Continuous flow synthesis of α-halo ketones: essential building blocks of antiretroviral agents.
V. D. Pinho (2014)
10.1002/9783527652891.CH06
Synthesis of Fine Chemicals
S. Hübner (2013)
10.1021/ol4027914
Continuous flow generation and reactions of anhydrous diazomethane using a Teflon AF-2400 tube-in-tube reactor.
F. Mastronardi (2013)
10.1126/science.1218781
Iron-Catalyzed Cyclopropanation in 6 M KOH with in Situ Generation of Diazomethane
B. Morandi (2012)
10.1021/OP200110A
Scalable in Situ Diazomethane Generation in Continuous-Flow Reactors
E. Rossi (2012)
Continuous production and reaction of a diazo compound
拉斐尔·威尔西玛斯·伊丽莎白·格西斯雷恩·雷特珍斯 (2011)
10.1002/anie.201101977
Continuous in situ generation, separation, and reaction of diazomethane in a dual-channel microreactor.
Ram Awatar Maurya (2011)
10.1007/7081_2009_22
Microreactor Technology as an Efficient Tool for Multicomponent Reactions
A. Cukalovic (2010)
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