Benzaldehyde → 3-(2-Aminoethyl)-5-(phenylmethylidene)-1,3-thiazolidine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

Benzaldehyde (63 μL, 0.62 mmol) and compound 29 (250 mg, 0.62 mmol) were dissolved in 10 mL of anhydrous ethanol at room temperature, and piperidine (7 μL, 0.062 mmol) was added to the reaction solution. The reaction mixture was stirred at 75° C. for 1 day and then allowed to cool down to room temperature until a yellow crystalline precipitate formed, and the solid was collected by filtration, washed with water and ethyl acetate, and dried to afford a white solid. Deprotection following the procedure of compound 6 gave the title compound 30a as a white solid (48.1%, 74 mg).

Provenance & Evidence