4-(Ethylamino)phenol → HCID 178516944, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of (4-hydroxy-phenyl)-ethylamine (3.14 g, 22.2 mmol) and Rhodanine (2.96 g, 22.2 mmol) in ethanol (314 mL) was added DIPEA (4.76 mL, 26.64 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (6.05 g, 22.2 mmol) was added in two portions within a period of 10 min. After addition, the suspension was allowed to warm to room temperature and stirred for 15 h. The resulting black solids were filtered through a plug of celite and washed with dichloromethane (200 mL) and methanol (500 mL). The combined solvents were removed under the vacuum and the crude residue was diluted with water (150 mL) and ethyl acetate (150 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution and dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent under the vacuum gave the crude residue which was purified by using Biotage silica gel column chromatography to afford 1.0 g (19% yield) of 2-[2-(4-hydroxy-phenyl)-ethylamino]-thiazol-4-one as a white amorphous solid: HRES(+) m/e calcd for C10H8ClFN2OS (M+H)+237.0692, found 237.0693.

Provenance & Evidence