European Journal of Chemistry

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



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Masaki Ichitani
Soh-ichi Kitoh
Keiko Tanaka
Shuhei Fujinami
Mitsuhiro Suda
Mitsunori Honda
Akio Kuwae
Kazuhiko Hanai
Ko-Ki Kunimoto

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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Ichitani, M.; Kitoh, S.- ichi; Tanaka, K.; Fujinami, S.; Suda, M.; Honda, M.; Kuwae, A.; Hanai, K.; Kunimoto, K.-K. Synthesis and Crystal Structure of (S)-5-Isopropyl-5-Methyl-2-Thiohydantoin. Eur. J. Chem. 2013, 4, 350-352.

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