

Synthesis and crystal structure of (S)-5-isopropyl-5-methyl-2-thiohydantoin
Masaki Ichitani (1)









(1) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(2) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(3) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(4) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(5) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(6) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(7) Graduate School of Natural Sciences, Nagoya City University, Mizuho-ku, Nagoya 467-8501, Japan
(8) Graduate School of Natural Sciences, Nagoya City University, Mizuho-ku, Nagoya 467-8501, Japan
(9) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(*) Corresponding Author
Received: 11 Jul 2013 | Accepted: 15 Jul 2013 | Published: 31 Dec 2013 | Issue Date: December 2013
Abstract
(S)-5-Isopropyl-5-methyl-2-thiohydantoin was synthesized by one-pot reaction of α-methyl-L-valine and thiourea in the absence of solvent. The crystal structure of this compound has been determined from single crystal X-ray diffraction data. This is the first report on the crystal structure of a homochiral 5-substituted 2-thiohydantoin with the unsubstituted NH groups. This compound, C7H12N2OS crystallizes in the chiral orthorhombic space group P212121 with four molecules in the unit cell. The unit cell parameters are: a = 8.2798(12) Å, b = 8.6024(13) Å, c = 12.826(2) Å and V = 913.6(2) Å3. In the crystals, the thioamide and amide N-H of one molecule are hydrogen-bonded to the thioamide C=S group of neighboring molecules to form rings with the R22(8) graph-set motif, and these rings are linked into infinite one-dimensional tapes.

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European Journal of Chemistry
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DOI: 10.5155/eurjchem.4.4.350-352.872
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Citations
[1]. Zeynep Pinar Haslak, Sesil Agopcan Cinar, Sevgi Sarigul Ozbek, Gérald Monard, Ilknur Dogan, Viktorya Aviyente
Elucidation of the atroposelectivity in the synthesis of axially chiral thiohydantoin derivatives
Organic & Biomolecular Chemistry 18(12), 2233, 2020
DOI: 10.1039/C9OB02556A

[2]. Masaki Ichitani, Soh-ichi Kitoh, Keiko Tanaka, Shuhei Fujinami, Mitsuhiro Suda, Mitsunori Honda, Ko-Ki Kunimoto
Crystal structures of racemic and enantiomeric 5-isopropyl-5-methylhydantoin
European Journal of Chemistry 5(1), 6, 2014
DOI: 10.5155/eurjchem.5.1.6-10.933

[3]. Gerzon E. Delgado, Luis E. Seijas, Asiloé J. Mora, Rafael Almeida, Teresa González
Crystal Structure of 2-Thiohydantoin-L-Isoleucine Synthesized under Solvent-Free Conditions
Molecular Crystals and Liquid Crystals 607(1), 192, 2015
DOI: 10.1080/15421406.2014.928433

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