Maleimide → HCID 12988939, compound

Participants

Reaction Steps

To a solution of maleimide (5.92 g, 61 mmol) in 200 ml of ethanol was added 4methoxybenzenethiol (7.5 ml, 61 mmol), and after 18 hours at room temperature the solvent was removed to give 3-(4-methoxy-phenylsulfanyl)pyrrolidine-2,5-dione, mp 93-94° C. This compound (5.0 g, 21 mmol) was oxidized with hydrogen peroxide, 30% in acetic acid, 220 ml to give 3-(4-methoxybenzenesulfonyl)pyrrolidine-2,5-dione as a white solid, mp 144-146° C. This compound was reacted with 1-chloro-4-(5-iodopent-1-ynyl)benzene in DMF using two equivalents of sodium bishexamethyldisilazide to give the title compound as colorless crystals, mp 160-162° C.; mass spectrum,(M−H) 444.2.

Provenance & Evidence