Triethylamine → Methyl 4-(1,1-dioxo-1lambda6-isothiazolidin-2-ylmethyl)benzoate

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Reaction Steps

Methyl 4-aminomethylbenzoate hydrochloride (1.61 g) and triethylamine (2.45 mL) were dissolved in dichloromethane (40 mL), 3-chloropropane-1-sulfonyl chloride (1.17 mL) was added under ice-cooling, and the mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was evaporated, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and 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) (1.46 mL) was added, and the mixture was stirred at room temperature overnight. To the reaction mixture was added 0.5N hydrochloric acid, and the mixture was extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:ethyl acetate) to give the title compound (1.95 g).

Provenance & Evidence