2,6-Dichlorobenzoic acid → HCID 19424407, compound

Participants

Reaction Steps

To a solution of 2-chloromethyl-4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (0.5 g; 2.08 mmol) in 10 ml of DMF was added at room temperature 2,6-dichlorobenzoic acid (0.44 g; 2.3 mmol), potassium carbonate (0.43 g, 3.1 mmol), and tetrabutylammonium bromide (67 mg; 0.21 mmol) and the resulting solution was allowed to react at 60°-70° C. for 2 hours and then cooled. The mixture was diluted with ice/water, extracted with ether/ethyl acetate (5:1, 400 ml), and the organic layer was washed with water, brine, and dried. The organic solution was concentrated in vacuo and the residue was purified by flash chromatography to afford 0.51 g (62%) of 2-(2,6-dichlorophenylcarbonyloxymethyl)-4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: Ar=2,6-Cl2 -phenyl; R1 =H; R2 =isopropyl; R3 =methyl) as a solid, m.p. 70°-71.5° C.

Provenance & Evidence