3,4-Dichlorophenol → HCID 85055384, compound

Participants

Reaction Steps

5-(4-Carboxybenzylidene)thiazolidine-2,4-dione (from Example 8, Step A) was dissolved in SO2Cl2 followed by addition of 1-2 drops of DMF. This resulting mixture was heated to ˜80° C. for 15-30 min at which time the reaction was concentrated under reduced pressure. The residue was dissolved in THF and added drop wise to a solution of 3,4-dichlorophenol (1.5 eq) and TEA (2 eq). This resulting mixture was stirred for additional 1-2 h at which time the solid in the reaction mixture was filtered off. The filtrate was concentrated under reduced pressure to yield solid that was washed with water and ether to afford pure ester. Alternatively, to a solution of 5-(4-carboxybenzylidene)thiazolidine-2,4-dione (1 eq) and 3,4-dichlorophenol (1 eq) in CH2Cl2 was added DCC (1 eq). The resulting reaction mixture was stirred for 16 h at which time the reaction was filtered, the filtrate was washed with water and concentrated under reduced pressure to provide crude product that was purified by recystallization.

Provenance & Evidence