Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Reactions of Benzimidazoline-2-thione Derivatives

  • Lee Tae Ryong (Department of Chemistry, Seoul National University) ;
  • Kim Kyongtae (Department of Chemistry, Seoul National University)
  • Published : 19890200
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Abstract

Two properties of sodium naphthalenide (2), i.e. a strong base and a good electron donor were utilized for one pot synthesis: 2-alkylthiobenzimidazoles were synthesized in excellent yields from the reactions of benzimidazoline-2-thione (1) with an equimolar amount of alkyl halides in the presence of 2. Continuous addition of a different alkyl halide without the isolation of 2-alkylthiobenzimidazoles afforded 1-alkyl-2-alkylthiobenzimidazoles having different alkyl groups at N and S atoms in excellent yields. Further addition of 2 to 1-alkyl-2-alkylthiobenzimidazoles gave excellent yields of 1-alkylbenzimidazoline-2-thiones. When 2 in THF was added to a suspension of 1-alkyl-2-alkylthiobenzimidazoles in THF, a bond cleavage between N and C of alkyl group as well as S and C of alkyl group occurred. This is in contrast to the observation in which only cleavage between S and C of alkyl group takes place in the homogeneous solution.

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  1. ChemInform Abstract: Synthesis and Reactions of Benzimidazoline‐2‐thione Derivatives. vol.20, pp.31, 1989, https://doi.org/10.1002/chin.198931142