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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
(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). Rxn with isothiocyanic acid gives the imidazole-2-thiol (5). {The sequence may involve first hydrolysis of the formamido group, followed by addn of the amine to isothiocyanic acid; cyclization of the thiourea nitrogen with the formyl function would complete formation of the heterocycle.} Desulfurization by means Raney-Nickel finishes the synthesis of ethnonam (6).

References

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.

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