Reaction of Benzoxazoline-2-thiones with Alkyl Halides

Masatoshi Yamato, Yasuo Takeuchi, Kuniko Hashigaki, Takashi Hirota

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)


The effect of the solvent on the reaction of benzoxazoline-2-thiones with alkyl halides was studied. The reaction of 1 with alkyl halides and potassium carbonate in dimethylformamide (DMF) gave the corresponding 2-alkylthiobenzoxazoles (2), but the same reaction gave 2-methoxybenzoxazoles (4a) when methanol was used in place of DMF as the solvent. On the other hand, the reaction of 1, methyl iodide, alcohol, and sodium hydride in tetrahydrofuran (THF) gave 2-[N-(dialkoxymethylene)amino]phenols (5).

Original languageEnglish
Pages (from-to)733-736
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Issue number2
Publication statusPublished - 1983


  • 2-[N-(dialkoxy-methylene)amino]phenol
  • 2-alkoxybenzoxazole
  • alkylation
  • benzoxazoline-2-thione
  • solvent effect

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery


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