Diisopropylethylamine → HCID 178516942, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of thiophen-2-yl-methylamine (22.63 g, 200 mmol) and rhodanine (2-thio-4-thiazolin-4-one) (13.32 g, 100 mmol) in acetonitrile (200 mL) was added DIEA (N,N-diisopropylethylamine) (34.8 mL, 45.0 mmol) at room temperature. Then, it gave a clear solution within 2 min and this solution was cooled to 0° C. To this, mercuric chloride (27.15 g, 100 mmol) was added in three portions within a period of 15 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 dichloromethane (500 mL) and methanol (1.0 L). The combined solvents were removed under the vacuum and the crude residue was diluted with water (250 mL) and ethyl acetate (250 mL). The two layers were separated and the aqueous layer was extracted with dichloromethane (2×250 mL). The two organic extracts were washed separately 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 solid. This solid was dissolved in acetonitrile (˜100 mL) at hot condition and then stored in the refrigerator overnight. The solids were collected by filtration and washed with cold acetonitrile (20 mL). After drying in air, 12.32 g (58% yield) of 2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one was isolated as a white amorphous solid: EI-HRMS m/e calcd for C8H8N2OS2 (M+) 212.0078, found 212.0083.

Provenance & Evidence