Diisopropylethylamine → HCID 178425042, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-6-methylbenzylamine (650 mg, 4.2 mmol) and Rhodanine (559 mg, 4.2 mmol) in acetonitrile (25 mL) was added DIPEA (1.74 mL, 10 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (1.22 g, 4.5 mmol) was added in one portion. After addition, the suspension was allowed to warm to room temperature and stirred for 3 days. The resulting black solids were filtered through a plug of celite and washed with dichloromethane (500 mL) and methanol (250 mL). The combined solvents were removed under the vacuum and the crude residue was dissolved in ethyl acetate (25 mL) at hot condition and stored in the refrigerator overnight. Then, the solids were collected by filtration and washed with ethyl acetate. After drying in air, 305 mg (28.5% yield) of 2-(2-chloro-6-methylbenzylamino)-thiazol-4-one was isolated as a white amorphous solid: EI-HRMS m/e calcd for C11H11ClN2OS (M+) 254.0281. found 254.0282.

Provenance & Evidence