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Lysidine (chemical)

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Lysidine
Skeletal formula of lysidine
Ball-and-stick model of the lysidine molecule
Names
Preferred IUPAC name 2-Methyl-4,5-dihydro-1H-imidazole
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.816 Edit this at Wikidata
EC Number
  • 208-596-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H8N2/c1-4-5-2-3-6-4/h2-3H2,1H3,(H,5,6)Key: VWSLLSXLURJCDF-UHFFFAOYSA-N
SMILES
  • CC1=NCCN1
Properties
Chemical formula C4H8N2
Molar mass 84.12 g/mol
Melting point 87 °C (189 °F; 360 K) (decomposes)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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.

References

  1. Lysidine at Sigma-Aldrich
  2. "Lysidine". pubchem.ncbi.nlm.nih.gov. Retrieved 13 December 2021.
  3. 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.
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