Journal of the Korean Magnetic Resonance Society (한국자기공명학회논문지)

Korean Magnetic Resonance Society (한국자기공명학회)
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Synthesis of substituted urea or benzimidazolone using 1,1'- carbonyldiimidazole and substituted anilines

  • Kyounghoon Lee (Department of Chemical Education and Research Institute of Natural Sciences, Gyeongsang National University)
  • Received : 2024.07.23
  • Accepted : 2024.08.07
  • Published : 2024.09.20
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Abstract

1,1'-carbonyldiimidazole (CDI) is a versatile reagent that can be used for synthesizing a variety of organic compounds containing carbonyl functional groups. The reactivity of CDI with two ortho-substituted anilines was tested and characterized with analytic techniques such as NMR, IR, and ESIMS. A reaction of CDI with two equivalents of disubstituted aniline (N1,N1-diethylbenzene-1,2-diamine) formed a urea compound, 1,3-bis(2-(diethylamino)phenyl)urea (1). On the other hand, a reaction with one equivalent of mono-substituted aniline (tert-butyl (2-aminophenyl)carbamate) formed a substituted benzimidazolone, tert-butyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-1-carboxylate (2). These results demonstrated that a singly substituted aniline prefers an intramolecular ring formation while an N,N-doubly-substituted aniline prefers a urea formation.

Keywords

Acknowledgement

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Education (RS-2023-00245147).

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