Institute of Chemistry, Slovak Academy of Sciences, Dubravska cesta 9,
SK-84238 Bratislava, Slovak Republic.
Tel. +421-7-378-2540, Fax +421-7-375565 ([email protected])
Received: 28 October 1997 / Published: 18 November 1997
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.
References and Notes
1. Ettlinger, M. G. J. Am. Chem. Soc. 1950, 72, 4792.
2. Sainsbury, M. in Ansell, M. F. (Ed.), Rodd's Chemistry of Carbon
Compounds, 2nd edn., Vol. IV, Part C, Elsevier, Amsterdam, 1986, p.
303.
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