Lysidine (chemical)

Lysidine^[1]

Names
IUPAC name 2-Methyl-4,5-dihydro-1H-imidazole
Identifiers
CAS Number	534-26-9
3D model (Jmol)	Interactive image
ChemSpider	10341
ECHA InfoCard	100.007.816
EC Number	208-596-6
PubChem	10798
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
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.