Hydrochloric Acid → 4-(1,1-Dioxo-1,2-thiazolidin-2-yl)benzoic acid

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Reaction Steps

Ethyl 4-aminobenzoate (0.92 g) and triethylamine (1.5 mL) were dissolved in dichloromethane (10 mL), 3-chloropropane-1-sulfonyl chloride (0.9 mL) was added under ice-cooling, and the mixture was stirred at room temperature overnight. After completion of the reaction, 1N hydrochloric acid was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was dissolved in N,N-dimethylformamide (8 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (1 mL) was added, and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue (1.5 g) was dissolved in ethanol (20 mL), 1N aqueous sodium hydroxide solution (8.4 mL) was added, and the mixture was stirred at 60° C. for 3 hr. To the reaction mixture were added 1N hydrochloric acid (9.2 mL) and water, and the precipitate was collected by filtration to give the title compound (0.98 g).

Provenance & Evidence