Lysidine (chemical)

Lysidine ^[1]

Names
Preferred IUPAC name 2-Methyl-4,5-dihydro-1H-imidazole
Identifiers
CAS Number	534-26-9  Y
3D model (JSmol)	Interactive image
ChemSpider	10341  Y
ECHA InfoCard	100.007.816
EC Number	208-596-6
PubChem CID	10798
UNII	987F50E3PE  Y
CompTox Dashboard (EPA)	DTXSID2060204
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: [2]
Pictograms
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 [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

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. ^[3]

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.