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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 8
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Original Articles

A Simple Synthesis of Certain Unsymmetrically Substituted N, N'-Dialkylthioureas

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Pages 891-897 | Published online: 19 Dec 2006

References

  • Duus , F. 1979 . Comprehensive Organic Chemistry , Edited by: Barton , D. and Ollis , W. D. Vol. 3 , 452 – 456 . New York : Pergamon Press . and references cited therein
  • Hodgkins , J. E. , Reeves , W. P. and Liu , Y.-T. G. 1961 . J. Am. Chem. Soc. , 83 : 2532
  • Hodgkins , J. E. and Ettlinger , M. G. 1956 . J. Org. Chem. , 29 : 404
  • This distillation is carried out in order to remove any remaining carbon disulfide. If carbon disulfide is not removed, all the ingredients required for formation of the undesired 1c are present (note Eqs. 2, 3, 4, and 1).
  • Determined by reverse phase HPLC analysis with external standard: Zorbax® ODS (SiO2-C18), 3:1 (v/v) acetonitrilemethanol, uv detection at 254 nm. We are grateful to Ms. Judy Knarr for performing these analyses.
  • Spectroscopic data: ir (neat) ν3250, 1660, 1345 cm−1; 1H nmr (60 MHz) (CDCl3) δ6.1–6.6 (m, 2H) 4.20 (m, 1H), 3.42 (broad q, J=6 Hz, 2H), 0.6–2.0 (m, 29H); 13C nmr (CDCl3) δ180.8, 50.4, 44.5, 36.9, 31.8, 29.4, 29.3, 27.1, 25.8, 22.7, 20.7, 14.1; ms 286 (M+
  • Takami , F. , Tokuyama , K. , Wakahara , S. and Maeda , T. 1973 . Chem. Pharm. Bull., Tokyo , 21 : 1311
  • The results of Takami, et al., (Ref. 6) do not support the alternative hypothesis that the rate of isothiocyanate formation (note Eq. 4) is dependent on the size of R'.
  • Robbins , J. D. U. S. Patent . 4,418,210 . 1983 . to Stauffer Chemical Co.
  • Darum , H. , Goetzschel , K. , Junghans , K. , Kochmann , W. , Pallas , M. , Walek , W. and Schnelle , W. E. German Patent . 150, 460 . 1981 . to VEB Chemiekombinat Bitterfeld.

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