Diethyl Ether → 1-Hydroxy-1-(1-methylethyl)-3-[4-(methylthio)phenyl]urea

Participants

Reaction Steps

N-Isopropylhydroxylamine hydrochloride (1.35 g, 12.1 mnmol) was dissolved in water (2 mL) then combined with diethyl ether (25 mL) followed by the addition of a solution of sodium hydroxide (0.48 g, 12.1 mmol) in water (2 mL). The reaction mixture was allowed to stir for several minutes then 4-(methylthio)phenyl isocyanate (2.0 g, 12.1 mmol) was added via pipette. A white precipitate formed. The reaction mixture was allowed to stir at ambient temperature overnight. The solid was isolated by filtration then dissolved in hot ethyl acetate. The ethyl acetate solution was dried over magnesium sulfate then concentrated under vacuum. The precipitate was collected and dried to afford 1.60 g of the desired product as a crystalline solid, m.p. 150.0°-150.3° C. Analysis: Calculated for C11H16N2O2S: %C, 54.98; %H, 6.71; %N, 11.66; Found: %C, 54.96; %H, 6.53; %N, 11.61.

Provenance & Evidence