Catalyst- and solvent-free synthesis of 2-fluoro-N- (3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide through a microwave-assisted Fries rearrangement: X-ray structural and theoretical studies

R. Moreno-Fuquen, K. Arango-Daraviña, D. Becerra, J.-C. Castillo, A. R. Kennedy, M. A. Macías

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Abstract

An efficient approach for the regioselective synthesis of (5-amino-3-methylsulfanyl- 1H-1,2,4-triazol-1-yl)(2-fluorophenyl)methanone, C10H9FN4OS, (3), from the N-acylation of 3-amino-5-methylsulfanyl-1H-1,2,4-triazole, (1), with 2-fluorobenzoyl chloride has been developed. Heterocyclic amide (3) was used successfully as a strategic intermediate for the preparation of 2-fluoro-N-(3- methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide, C10H9FN4OS, (4), through a microwave-assisted Fries rearrangement under catalyst- and solvent-free conditions. Theoretical studies of the prototropy process of (1) and the Fries rearrangement of (3) to provide (4), involving the formation of an intimate ion pair as the key step, were carried out by density functional theory (DFT) calculations. The crystallographic analysis of the intermolecular interactions and the energy frameworks based on the effects of the different molecular conformations of (3) and (4) are described.
Original languageEnglish
Pages (from-to)359-371
Number of pages13
JournalActa Crystallographica Section C: Structural Chemistry
VolumeC75
Issue numberPart 3
Early online date20 Feb 2019
DOIs
Publication statusPublished - 1 Mar 2019

Keywords

  • Fries rearrangement
  • heterocyclic amides
  • crystal structure
  • amino-1,2,4-triazole
  • prototropy process
  • microwave-assisted reaction
  • DFT
  • computational chemistry
  • Hirshfeld surface maps

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