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Strategic Application of Residence-Time Control in Continuous-Flow Reactors.

Mándity IM, Ötvös SB, Fülöp F - ChemistryOpen (2015)

Bottom Line: As a sustainable alternative for conventional batch-based synthetic techniques, the concept of continuous-flow processing has emerged in the synthesis of fine chemicals.Systematic tuning of the residence time, a key parameter of continuous-reaction technology, can govern the outcome of a chemical reaction by determining the reaction rate and the conversion and by influencing the product selectivity.Such a fine reaction control cannot be performed in conventional batch reaction set-ups.

View Article: PubMed Central - PubMed

Affiliation: Institute of Pharmaceutical Chemistry, University of Szeged Eötvös u. 6, H-6720, Szeged, Hungary.

ABSTRACT
As a sustainable alternative for conventional batch-based synthetic techniques, the concept of continuous-flow processing has emerged in the synthesis of fine chemicals. Systematic tuning of the residence time, a key parameter of continuous-reaction technology, can govern the outcome of a chemical reaction by determining the reaction rate and the conversion and by influencing the product selectivity. This review furnishes a brief insight into flow reactions in which high chemo- and/or stereoselectivity can be attained by strategic residence-time control and illustrates the importance of the residence time as a crucial parameter in sustainable method development. Such a fine reaction control cannot be performed in conventional batch reaction set-ups.

No MeSH data available.


CF synthesis of Rufinamide with precise residence-time control.18
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fig07: CF synthesis of Rufinamide with precise residence-time control.18

Mentions: One of the best-selling five-membered heterocyclic pharmaceuticals is Rufinamide, an antiepileptic drug that contains a 1,2,3-triazole moiety. Hessel and co-workers established a novel and sustainable CF technique for the synthesis of Rufinamide, which relies greatly on precise residence-time control to govern the sensitive balance between the decomposition of the starting materials and the acceleration of the reaction at elevated temperatures.18 The key step in the synthesis of Rufinamide is the 1,3-dipolar cycloaddition of 2,6-difluorobenzyl azide with an appropriate dipolarophile. (E)-Methyl 3-methoxyacrylate was utilized as a nontoxic and inexpensive dipolarophile which results in the selective formation of the desired 1,4-disubsituted 1,2,3-triazole regioisomer without the need for an added catalyst (Figure 7). To attain a higher reaction rate, solvent-free conditions were applied.


Strategic Application of Residence-Time Control in Continuous-Flow Reactors.

Mándity IM, Ötvös SB, Fülöp F - ChemistryOpen (2015)

CF synthesis of Rufinamide with precise residence-time control.18
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4522171&req=5

fig07: CF synthesis of Rufinamide with precise residence-time control.18
Mentions: One of the best-selling five-membered heterocyclic pharmaceuticals is Rufinamide, an antiepileptic drug that contains a 1,2,3-triazole moiety. Hessel and co-workers established a novel and sustainable CF technique for the synthesis of Rufinamide, which relies greatly on precise residence-time control to govern the sensitive balance between the decomposition of the starting materials and the acceleration of the reaction at elevated temperatures.18 The key step in the synthesis of Rufinamide is the 1,3-dipolar cycloaddition of 2,6-difluorobenzyl azide with an appropriate dipolarophile. (E)-Methyl 3-methoxyacrylate was utilized as a nontoxic and inexpensive dipolarophile which results in the selective formation of the desired 1,4-disubsituted 1,2,3-triazole regioisomer without the need for an added catalyst (Figure 7). To attain a higher reaction rate, solvent-free conditions were applied.

Bottom Line: As a sustainable alternative for conventional batch-based synthetic techniques, the concept of continuous-flow processing has emerged in the synthesis of fine chemicals.Systematic tuning of the residence time, a key parameter of continuous-reaction technology, can govern the outcome of a chemical reaction by determining the reaction rate and the conversion and by influencing the product selectivity.Such a fine reaction control cannot be performed in conventional batch reaction set-ups.

View Article: PubMed Central - PubMed

Affiliation: Institute of Pharmaceutical Chemistry, University of Szeged Eötvös u. 6, H-6720, Szeged, Hungary.

ABSTRACT
As a sustainable alternative for conventional batch-based synthetic techniques, the concept of continuous-flow processing has emerged in the synthesis of fine chemicals. Systematic tuning of the residence time, a key parameter of continuous-reaction technology, can govern the outcome of a chemical reaction by determining the reaction rate and the conversion and by influencing the product selectivity. This review furnishes a brief insight into flow reactions in which high chemo- and/or stereoselectivity can be attained by strategic residence-time control and illustrates the importance of the residence time as a crucial parameter in sustainable method development. Such a fine reaction control cannot be performed in conventional batch reaction set-ups.

No MeSH data available.