Ethonam

Ethonam
Identifiers
	IUPAC name Ethyl 3-(1,2,3,4-tetrahydronaphthalen-1-yl)imidazole-4-carboxylate;
CAS Number	15037-44-2 ;
PubChem CID	27007;
ChemSpider	49010;
UNII	G84P716Z93;
KEGG	D04085;
ChEMBL	ChEMBL25148;
CompTox Dashboard (EPA)	DTXSID30864551 ;
Chemical and physical data
Formula	C16H18N2O2
Molar mass	270.332 g·mol−1
	(verify)

Ethonam is an antifungal agent.

Synthesis

2-Aminotetralin () is alkylated with ethylchloroacetate to afford the glycine derivative. Heating with formic acid then affords the amide (2). This compound is then reacted with ethyl formate to yield hydroxymethylene ester (3). Reaction with isothiocyanic acid gives the imidazole-2-thiol (5). The sequence may first involve hydrolysis of the formamido group, followed by addition of the amine to isothiocyanic acid; cyclization of the thiourea nitrogen with the formyl function would complete formation of the heterocycle. Desulfurization by means of Raney nickel finishes the synthesis of ethonam (6).

References

^ Godefroi EF, Van Cutsem J, Van Der Eycken CA, Janssen PA (November 1967). "1-(1-indanyl)- and 1-(1-tetralyl)imidazole-5-carboxylate esters, a novel type of antifungal agents". Journal of Medicinal Chemistry. 10 (6): 1160–1. doi:10.1021/jm00318a039. PMID 6056048.

[1] Godefroi EF, Van Cutsem J, Van Der Eycken CA, Janssen PA (November 1967). "1-(1-indanyl)- and 1-(1-tetralyl)imidazole-5-carboxylate esters, a novel type of antifungal agents". Journal of Medicinal Chemistry. 10 (6): 1160–1. doi:10.1021/jm00318a039. PMID 6056048.