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Short Note

3-Dodecyl-5-methyl-2-oxazolidinthione

by
Bohumil Steiner
,
Jan Gajdos
and
Miroslav Koos
*
Institute of Chemistry, Slovak Academy of Sciences, Dubravska cesta 9, SK-84238 Bratislava, Slovak Republic
*
Author to whom correspondence should be addressed.
Molecules 1997, 2(11), M40; https://doi.org/10.3390/M40
Submission received: 28 October 1997 / Published: 18 November 1997
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 02 m40 i001
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): Rf 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

  1. Ettlinger, M. G. J. Am. Chem. Soc. 1950, 72, 4792. [CrossRef]
  2. 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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MDPI and ACS Style

Steiner, B.; Gajdos, J.; Koos, M. 3-Dodecyl-5-methyl-2-oxazolidinthione. Molecules 1997, 2, M40. https://doi.org/10.3390/M40

AMA Style

Steiner B, Gajdos J, Koos M. 3-Dodecyl-5-methyl-2-oxazolidinthione. Molecules. 1997; 2(11):M40. https://doi.org/10.3390/M40

Chicago/Turabian Style

Steiner, Bohumil, Jan Gajdos, and Miroslav Koos. 1997. "3-Dodecyl-5-methyl-2-oxazolidinthione" Molecules 2, no. 11: M40. https://doi.org/10.3390/M40

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