Solvent-free synthesis and crystal structure of rac-2-thiohydantoin-valine

Thiohydantoins have been used in the manufacture of medicines and in industrial processes. Depending on the nature and type of substitution on the heterocyclic ring, these compounds may display pharmaceutical and biological activity with a variety of applications as antiepileptic, antitumoral, antiinflammatory, and principally for the treatment of prostate cancer. In this study, a new thiohydantoin was synthetized from the valine amino acid and structurally characterized. The title compound, C₆H₁₀N₂O₂S, with systematic name rac-5-isopropyl-2-tioxoimidazolidin-4-one, has been synthetized by a solvent-free synthesis. The heterocyclic compound was characterized by spectroscopic infrared (FTIR) and nuclear magnetic resonance (NMR) techniques, powder and single-crystal X-ray diffraction analysis (XRD). This material crystallizes in the monoclinic space group P2₁/c. In the supramolecular structure, the molecules are joined by N-H···O and N-H···S hydrogen bonds, forming centrosymmetric R² ₂(8) dimers and C² ₂(9) chains that run along the [001] direction in an infinite one-dimensional network.