3-Dodecyl-5-methyl-2-oxazolidinthione

Bohumil Steiner; Jan Gajdos; Miroslav Koos

doi:10.3390/M40

,

and

Institute of Chemistry, Slovak Academy of Sciences, Dubravska cesta 9, SK-84238 Bratislava, Slovak Republic

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Author to whom correspondence should be addressed.

Molecules1997, 2(11), M40;https://doi.org/10.3390/M40

This article belongs to the Section Molbank Section of Molecules, 1997-2001

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Oxazolidin-2-thiones can be prepared by the cyclization reaction of corresponding beta-amino alcohols with carbon disulfide or thiophosgene [1,2].

A solution of carbon disulfide (1.60 g, 21 mmol) in dioxane (10 ml) was added dropwise to a cold (0deg.C) mixture of 1-dodecylamino-2-propanol (4.87 g, 20 mmol) and KOH (1.12 g, 20 mmol) in water (10 ml) under stirring for 15 min, during which the mixture warmed to room temperature and became yellow and homogeneous. Additional KOH (1.12 g, 20 mmol) in water (20 ml) and lead nitrate (3.65 g, 11 mmol) in water (20 ml) were then added and the suspension was stirred at 60 deg.C for 0.5 h. The orange precipitate was filtered off, washed with MeOH and the solvent evaporated. The product was recrystallized from hexane to give the title compound as white crystals (3.2 g, 56%).

M.p. 37-38 deg.C.

TLC (Hexane/EtOAc 2:1): R_f 0.53.

¹H-NMR (CDCl₃): 4.84 (m, J=9.6 and 7.8 and 6.3 Hz, 1H, H-5); 3.85 (t, J=9.6 Hz, 1H, H-4); 3.63 (m, 2H, CH₂N); 3.33 (dd, J=9.6 and 7.8 Hz, 1H, H-4'); 1.63 (m, 2H, CH₂CH₂N); 1.49 (d, J=6.3 Hz, 3H, CH₃); 1.33 (bs, 4H, 2 x CH₂); 1.26 (s, 14H, 7 x CH₂); 0.88 (t, J=6.7 Hz, 3H, CH₃).

¹³C-NMR (CDCl₃): 187.2 (C=S), 74.8 (C-5), 54.4 (C-4), 48.1 (CH₂N), 31.9, 29.6, 29.4, 29.3, 26.6, and 22.7 (the other CH₂ groups), 20.3 (CH₃ at C-5), 14.1 (CH₃).

Anal. calc. for C₁₆H₃₁NOS (285.49): C 67.31, H 10.94, N 4.91, S 11.23; found: C 67.13, H 10.99, N 4.97, S 11.15.

Acknowledgments: The authors would like to thank Scientific Grant Agency (VEGA, project No. 2/4144/97) for financial support.

Supplementary materials

Supplementary File 1Supplementary File 2

References and Notes

Ettlinger, M. G. J. Am. Chem. Soc. 1950, 72, 4792. [CrossRef]
Sainsbury, M. Ansell, M. F., Ed.; Rodd’s Chemistry of Carbon Compounds, 2nd edn.; Vol. IV, Part C; Elsevier: Amsterdam, 1986; p. 303. [Google Scholar]

Sample availability: Available from the authors and MDPI, MDPI Reg. No.13741.

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