Diisopropylethylamine → N-[(5-Methyl-2-phenyl-4-oxazolyl)methyl]-4-[(thiazolidine-2,4-dion-5-yl)methyl]benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

4-[(Thiazolidine-2,4-dion-5-yl)methyl]benzenesulfonyl chloride (1.62 g, 5.31 mmol) in 25 mL of CH2Cl2 was cooled to 0° C. N-[(5-Methyl-2-phenyl-4-oxazolyl)methyl]amine (1.0 g, 5.31 mmol) in 10 mL of CH2Cl2 was added dropwise, followed by diisopropylethylamine(1.1 mL, 6.37 mmol) and the mixture stirred at 0° C. for 20 minutes,then at room temperature for 18 hours. The reaction mixture was diluted with 20 mL CH2Cl2, washed 3×25 mL 1N HCl, 1×25 mL 5% NaHCO3 and 2×25 mL brine, dried (MgSO4) and stripped to1.9 g of solids. The latter was flash chromatographed on silica gel using 3:40 ethyl acetate:hexane as eluant to yield 0.34 g of purified, present title product, mp 120°-122° C.

Provenance & Evidence