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Influence of Polarity on the Scalability and Reproducibility of Solvent-Free Microwave-Assisted Reactions

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Organic reactions performed in the absence of solvent in domestic ovens without appropriate temperature control are generally considered as not reproducible, particularly when different instruments are used. For this reason, reproducibility has historically been one of the major issues associated with Microwave-Assisted Organic Synthesis (MAOS) especially when domestic ovens are involved. The lack of reproducibility limits the general applicability and the scale up of these reactions. In this work several solvent-free reactions previously carried out in domestic ovens have been translated into a single-mode microwave reactor and then scaled up in a multimode oven. The results show that most of these reactions, although not considered as reproducible, can be easily updated and applied in microwave reactors using temperature-controlled conditions. Furthermore, computational calculations can assist to explain and/or predict whether a reaction will be reproducible or not.

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Keywords: 1,3-Bis(4-methylthiophenyl)urea; 1-(3-Phenylpropyl)-1,2,3-benzotriazole; 2-(3-Phenylpropyl)-1,2,3-benzotriazole; 2-(4-Phenoxybutyl)-1,2,3-benzotriazole; B3LYP; MAOS; MILESTONE; Microwave-Assisted Organic Synthesis; Montmorillonite K10; PCM; PCM solvent model; SN2 pathway; Scalability; diarylurea; microwave-assisted reactions; monomode apparatus; multimode microwave reactor; p-nitrobenzyl bromide; reproducibility; solvent-free reactions

Document Type: Research Article

Publication date: February 1, 2011

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  • Combinatorial Chemistry & High Throughput Screening publishes full length original research articles and reviews describing various topics in combinatorial chemistry (e.g. small molecules, peptide, nucleic acid or phage display libraries) and/or high throughput screening (e.g. developmental, practical or theoretical). Ancillary subjects of key importance, such as robotics and informatics, will also be covered by the journal. In these respective subject areas, Combinatorial Chemistry & High Throughput Screening is intended to function as the most comprehensive and up-to-date medium available. The journal should be of value to individuals engaged in the process of drug discoveryand development, in the settings of industry, academia or government.
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