Lysidine (chemical)

From Wikipedia, the free encyclopedia
(Redirected from C4H8N2)
Jump to navigation Jump to search
Lysidine[1]
Skeletal formula of lysidine
Ball-and-stick model of the lysidine molecule
Names
Preferred IUPAC name
2-Methyl-4,5-dihydro-1H-imidazole
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number
  • 208-596-6
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C4H8N2/c1-4-5-2-3-6-4/h2-3H2,1H3,(H,5,6)
    Key: VWSLLSXLURJCDF-UHFFFAOYSA-N
  • CC1=NCCN1
Properties
C4H8N2
Molar mass 84.12 g/mol
Melting point 87 °C (189 °F; 360 K) (decomposes)
Hazards
GHS labelling:[2]
GHS07: Exclamation mark
Warning
H315, H319, H335
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).

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

[edit | edit source]

It is prepared by condensing ethylenediamine with acetic acid to give the diamide, which undergoes CaO-induced cyclization. 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]

File:Synthesis of metronidazole.png

References

[edit | edit source]
  1. ^ Lysidine at Sigma-Aldrich
  2. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  3. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).