Maleimide → HCID 12988939, compound

Participants

Reaction Steps

To a solution of maleimide (5.92 g, 61 mmol) in 200 ml of ethanol was added 4-methoxybenzenethiol (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-(5iodopent-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