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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Editor-in-Chief
European Journal of Chemistry

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
/


[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
/


References


[1]. Mutschler, E.; Derendorf, H. Drug Actions, Basic Principles and Therapeutic Aspects, Medpharm Scientific Publishers, Stuttgart, 1995.
PMCid:PMC1908869

[2]. Knabe, J.; Baldauf, J.; Ahlhem, A. Pharmazie 1997, 52, 912-919.
PMid:9480456

[3]. Singh, G.; Driever, P. H.; Sander, J. W. Brain 2005, 128, 7-17.
http://dx.doi.org/10.1093/brain/awh363
PMid:15574465

[4]. Carmi, C.; Cavazzoni, A.; Zuliani, V.; Lodola, A.; Bordi, F.; Plazzi, P. V.; Alfieri, R. R.; Petronini, P. G.; Mor, M. Bioorg. Med. Chem. Lett. 2006, 16, 4021-4025.
http://dx.doi.org/10.1016/j.bmcl.2006.05.010
PMid:16713265

[5]. Wang, Z. D.; Sheikh, S. O.; Zhang, Y. Molecules 2006, 11, 739-750.
http://dx.doi.org/10.3390/11100739
PMid:17971750

[6]. Jha, S.; Silversides, J. D.; Boyle, R. W.; Archibald, S. J. CrystEngComm 2010, 12, 1730-1739.
http://dx.doi.org/10.1039/b924683e

[7]. Cruz-Cabeza, A. J.; Schwalbe, C. H. New J. Chem. 2012, 36, 1347-1354.
http://dx.doi.org/10.1039/c2nj21060f

[8]. Ogawa, T.; Kitoh, S.; Ichitani, M.; Kuwae, A.; Hanai, K.; Kunimoto, K. K. Anal. Sci. X-ray Struct. Anal. Online 2007, 23, x199-x200.
http://dx.doi.org/10.2116/analscix.23.x199

[9]. Ogawa, T.; Kitoh, S.; Okagawa, M.; Ichitani, M.; Kuwae, A.; Hanai, K.; Kunimoto, K. K. Anal. Sci. X-ray Struct. Anal. Online 2007, 23, x201-x202.
http://dx.doi.org/10.2116/analscix.23.x201

[10]. Kunimoto, K.-K.; Ichitani, M.; Ogawa, T.; Kitoh, S.; Kuwae, A.; Hanai, K. Spectrosc. Lett. 2009, 42, 73-80.
http://dx.doi.org/10.1080/00387010802428575

[11]. Ogawa, T.; Okumura, H.; Honda, M.; Suda, M.; Fujinami, S.; Kuwae, A.; Hanai, K.; Kunimoto, K. K. Anal. Sci. X-ray Struct. Anal. Online 2009, 25, 91-92.
http://dx.doi.org/10.2116/xraystruct.25.91

[12]. Taniguchi, K.; Okumura, H.; Honda, M.; Suda, M.; Fujinami, S.; Kuwae, A.; Hanai, K.; Maeda, S.; Kunimoto, K. K. Anal. Sci. X-ray Struct. Anal. Online 2009, 25, 93-94.
http://dx.doi.org/10.2116/xraystruct.25.93

[13]. Ichitani, M.; Kitoh, S.; Fujinami, S.; Honda, M.; Suda, M.; Kunimoto, K. K. Acta Cryst. E 2013, 69, o953-o953.
http://dx.doi.org/10.1107/S1600536813013639
PMid:23795113 PMCid:PMC3685094

[14]. Rigaku CrystalClear, Rigaku Corporation, Tokyo, Japan, 2006.

[15]. Rigaku REQAB, Rigaku Corporation, Tokyo, Japan, 1998.

[16]. Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; Caro, L.; Giacovazzo, C.; Polidori, G.; Siliqi, D.; Spagna, R. J. Appl. Cryst. 2007, 40, 609-613.
http://dx.doi.org/10.1107/S0021889807010941

[17]. Sheldrick, G. M. Acta Crystallogr. A 2008, 64, 112-122.
http://dx.doi.org/10.1107/S0108767307043930
PMid:18156677

[18]. Rigaku CrystalStructure, Rigaku Corporation, Tokyo, Japan, 2010.

[19]. Flack, H. D. Acta Crystallogr. A 1983, 39, 876-881.
http://dx.doi.org/10.1107/S0108767383001762

[20]. Farrugia, L. J. J. Appl. Cryst. 2012, 45, 849-854.
http://dx.doi.org/10.1107/S0021889812029111

[21]. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Cryst. 2006, 39, 453-457.
http://dx.doi.org/10.1107/S002188980600731X

[22]. Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126.
http://dx.doi.org/10.1021/ar00172a005


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. 4 Oct. 2023
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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