Diethyl Ether → HCID 21936578, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-ethyl-4-aminobenzonitrile (1.35 g, 9.29 mmol) in DMF (10 mL) at room temperature was added sodium hydride (0.28 g, 80%, 9.29 mmol). The mixture was heated to 70° C. for 40 minutes and was then cooled to room temperature. A solution of tert-amyl isothiocyanate (1.0 g, 7.74 mmol) in DMF (1 mL) was added by syringe and the reaction was stirred at 70° C. overnight. The cooled reaction mixture was diluted with 2N HCl and water and the mixture was extracted with ethyl acetate. The organic phase was dried and concentrated to afford an oil. The crude product was taken up in a minimal amount of diethyl ether and the solution was made turbid by adding petroleum ether. Sonication resulted in the formation of a precipitate which was collected by filtration to afford 1.2 g (56%) of 1-(2-ethyl-4-cyanophenyl)-3-(1,1-dimethyl-propyl)-thiourea as an off-white solid which was used without further purification.

Provenance & Evidence