Lysidine (chemical)

Lysidine[1]
Skeletal formula of lysidine
Ball-and-stick model of the lysidine molecule
Names
IUPAC name
2-Methyl-4,5-dihydro-1H-imidazole
Identifiers
534-26-9 YesY
3D model (Jmol) Interactive image
ChemSpider 10341
ECHA InfoCard 100.007.816
EC Number 208-596-6
PubChem 10798
Properties
C4H8N2
Molar mass 84.12 g/mol
Melting point 87 °C (189 °F; 360 K) (decomposes)
Hazards
R-phrases R36/37/38
S-phrases S26 S37/39
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Lysidine is a derivative of 2-imidazoline derivative. 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.

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.


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