Diisopropylethylamine → HCID 178516943, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-fluoro phenethylamine (3.06 g, 22 mmol) and Rhodanine (2.66 g, 20 mmol) in acetonitrile (70 mL) was added DIPEA (7.66 mL, 44 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (5.97 g, 22 mmol) was added in two portions within 10 min. After addition, the suspension was allowed to warm to room temperature and stirred for 2 days. The resulting black solids were filtered through a plug of celite and washed with acetonitrile (1.0 L) and ethyl acetate (500 mL). The combined solvents were removed under the vacuum and the crude residue was dissolved in ethyl acetate (100 mL) and water (100 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined extracts were washed with brine solution and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the filtrate was removed under the vacuum and the crude residue was dissolved in acetonitrile (25 mL) at hot condition. After cooling in the refrigerator overnight, the solids were collected by filtration and washed with acetonitrile. After drying in air, 3.65 g (76.6% yield) of 2-[2-(3-fluoro-phenyl)-ethylamino]-thiazol-4-one was isolated as a white solid: HRES(+) m/e calcd for C11H11FN2OS (M+H)+ 239.0649. found 239.0647.

Provenance & Evidence