Lysidine (chemical)

Lysidine is a derivative of 2-imidazoline. It is a colorless solid with basic properties and soluble in organic solvents. It is used as a precursor to other compounds of pharmaceutical interest.

Lysidine[1]
Names
IUPAC name
2-Methyl-4,5-dihydro-1H-imidazole
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.816
EC Number
  • 208-596-6
UNII
Properties
C4H8N2
Molar mass 84.12 g/mol
Melting point 87 °C (189 °F; 360 K) (decomposes)
Hazards
R-phrases (outdated) R36/37/38
S-phrases (outdated) S26 S37/39
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Synthesis and reactions

It is prepared by condensing ethylenediamine with acetic acid to give the diamide, which undergoes CaO-induced cyclization. Alternatively, it arises from the condensation of glyoxal, acetaldehyde, and ammonia.

Lysidine is an intermediate in the synthesis of the drug metronidazole. In the presence of Raney nickel, it undergoes dehydrogenation to 2-methylimidazole, which can then be further elaborated.[2]

References

  1. Lysidine at Sigma-Aldrich
  2. Kraft, M. Ya.; Kochergin, P. M.; Tsyganova, A. M.; Shlikhunova, V. S. (1989). "Synthesis of metronidazole from ethylenediamine". Pharmaceutical Chemistry Journal. 23 (10): 861. doi:10.1007/BF00764821. S2CID 38187002.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.