European Journal of Chemistry 2013, 4(4), 350-352 | doi: https://doi.org/10.5155/eurjchem.4.4.350-352.872 | Get rights and content






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


Masaki Ichitani (1) , Soh-ichi Kitoh (2) , Keiko Tanaka (3) , Shuhei Fujinami (4) , Mitsuhiro Suda (5) , Mitsunori Honda (6) , Akio Kuwae (7) , Kazuhiko Hanai (8) , Ko-Ki Kunimoto (9,*)

(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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Keywords


Thiourea; Homochiral; Hydrogen-bond; Crystal structure; 2-Thiohydantoin; 2-Thioxoimidazolidin-4-one

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DOI: 10.5155/eurjchem.4.4.350-352.872

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Citations

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[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
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[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
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[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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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Ichitani, M.; Kitoh, S.; Tanaka, K.; Fujinami, S.; Suda, M.; Honda, M.; Kuwae, A.; Hanai, K.; Kunimoto, K. Eur. J. Chem. 2013, 4(4), 350-352. doi:10.5155/eurjchem.4.4.350-352.872
Ichitani, M.; Kitoh, S.; Tanaka, K.; Fujinami, S.; Suda, M.; Honda, M.; Kuwae, A.; Hanai, K.; Kunimoto, K. Synthesis and crystal structure of (S)-5-isopropyl-5-methyl-2-thiohydantoin. Eur. J. Chem. 2013, 4(4), 350-352. doi:10.5155/eurjchem.4.4.350-352.872
Ichitani, M., Kitoh, S., Tanaka, K., Fujinami, S., Suda, M., Honda, M., Kuwae, A., Hanai, K., & Kunimoto, K. (2013). Synthesis and crystal structure of (S)-5-isopropyl-5-methyl-2-thiohydantoin. European Journal of Chemistry, 4(4), 350-352. doi:10.5155/eurjchem.4.4.350-352.872
Ichitani, Masaki, Soh-ichi Kitoh, Keiko Tanaka, Shuhei Fujinami, Mitsuhiro Suda, Mitsunori Honda, Akio Kuwae, Kazuhiko Hanai, & Ko-Ki Kunimoto. "Synthesis and crystal structure of (S)-5-isopropyl-5-methyl-2-thiohydantoin." European Journal of Chemistry [Online], 4.4 (2013): 350-352. Web. 30 May. 2020
Ichitani, Masaki, Kitoh, Soh-ichi, Tanaka, Keiko, Fujinami, Shuhei, Suda, Mitsuhiro, Honda, Mitsunori, Kuwae, Akio, Hanai, Kazuhiko, AND Kunimoto, Ko-Ki. "Synthesis and crystal structure of (S)-5-isopropyl-5-methyl-2-thiohydantoin" European Journal of Chemistry [Online], Volume 4 Number 4 (31 December 2013)

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DOI Link: https://doi.org/10.5155/eurjchem.4.4.350-352.872

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