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Synthesis of isothiocyanates

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A facile and general protocol for the preparation of isothiocyanates from alkyl and aryl amines relies on a tosyl chloride mediated decomposition of a dithiocarbamate salts that are generated in situ by treatment of amines with carbon disulfide and triethylamine. Vairous alkyl- and arylisothiocyanates have been prepared in good yield.
R. Wong, S. J. Dolman, J. Org. Chem., 2007, 72, 3969-3971.


A two-step, one-pot reaction of primary amines or their salts with carbon disulfide, followed by reaction of the intermediate dithiocarbamates with T3P provides isothiocyanates in good yields. T3P (propane phosphonic acid anhydride) acts as an efficient desulfurating agent.
Ł Janczewski, A. Gajda, S. Frankowski, T. M. Goszczyński, T. Gajda, Synthesis, 2018, 50, 1141-1151.


A facile and efficient synthesis of isothiocyanates involves the reaction of amines with phenyl chlorothionoformate in the presence of solid sodium hydroxide by either a one-pot process or a two-step approach. The one-pot process is useful for preparing alkyl and electron-rich aryl isothiocyanates, whereas the two-step approach is more versatile.
Z.-Y. Li, H.-Z. Ma, C. Han, H.-T. Xi, Q. Meng, X. Chen, X.-Q. Sun, Synthesis, 2013, 45, 1667-1674.