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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 10, Number 1
BKCSDE 10(1)
January 20, 1989 

Synthesis and Reactions of Benzimidazoline-2-thione Derivatives
Tae Ryong Lee, Kyongtae Kim*
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.
80 - 84
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