Ethanol → HCID 15104318, compound

Participants

Reaction Steps

1.4 g of NaNO2 in 30 ml of water are added dropwise with ice cooling in the course of about 20 minutes to 7 g (0.02 mol) of 2-methyl-5-ethoxycarbonyl-4-(4-amino-3-trifluoromethyl-phenoxy)-thiazole (cf. Example (IV-4) in 40 ml of concentrated hydrochloric acid. After the mixture has been stirred for 5 minutes, 300 ml of ethanol are added, and the mixture is then heated slowly to reflux temperature and refluxed for 30 minutes. The volatile constituents are subsequently removed in vacuo, the oil which remains is then taken up in 50 ml of water, a pH of 8 is established by adding dilute sodium hydroxide solution, the mixture is extracted twice with dichloromethane, the extract is dried (over MgSO4) and evaporated in vacuo, and the crude product which remains is filtered chromatographically through silica gel (eluent: toluene). 5.6 g (83.6 % of theory) of 2-methyl-5-ethoxycarbonyl-4-(3-trifluoromethyl-phenyloxy)-thiazole are obtained; melting point: 56° C.

Provenance & Evidence