2,6-Dichlorobenzoic acid → 2-(2,6-Dichlorophenylcarbonyloxymethyl)-4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Participants

Reaction Steps

To a solution of 2-chloromethyl-4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (0.41 g; 1.35 mmol) in DMF was added at room temperature 2,6-dichlorobenzoic acid (0.283 g; 1.48 mmol) and potassium carbonate (0.246 g, 1.78 mmol), and the resulting solution was allowed to react at room temperature for 40 hours. The mixture was poured into ice/water, extracted with ethyl acetate, and the organic layer was washed with water, brine, and dried. The organic solution was concentrated in vacuo and the residue was purified by silica column chromatography to afford 62 mg (10%) of 2-(2,6-dichlorophenylcarbonyloxymethyl) -4- (3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: Ar=2, 6-Cl2 -phenyl; R1 =H; R2 =(CH2)2C (Cl) (CH3)2 ; R3 =CH3) as a gum.

Provenance & Evidence