Diethyl Carbonate → HCID 15591328, compound

Participants

Reaction Steps

1.3 g of 3-(4-cyanophenyl)-5-[4-(1,2-diethoxycarbonylethyl)piperazinomethyl)oxazolidin-2-one [obtainable by reaction of 4-cyanoaniline with 2,3-epoxypropan-1-ol to give N-[4-cyanophenyl]-2,3-dihydroxypropylamine, reaction with diethyl carbonate in the presence of K tert-butoxide to give 3-(4-cyano-phenyl)-5-hydroxymethyloxazolidin-2-one, subsequent esterification with methanesulfonyl chloride and reaction with "B"] and 1.1 g of hydroxylamine hydrochloride are boiled for 2 hours in 125 ml of ethanol in the presence of 2.24 g of sodium ethoxide. The reaction mixture is then filtered and concentrated in vacuo. The residue is dissolved in water, the solution is adjusted to pH 3 using 2N hydrochloric acid and the resulting precipitate is filtered off with suction. After recrystallizing from water/glacial acetic acid, 3-[4-amino(hydroxyimino)methylphenyl]-5-[4-(1,2-diethoxycarbonylethyl)piperazinomethyl]oxazolidin-2-one, m.p. 186°, is obtained.

Provenance & Evidence