Maleimide → HCID 12988939, compound

HRID 982742Notes

Reaction equation

HRID 982742 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH:3]=[CH:2]1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1>C(O)C>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][CH:2]2[CH2:3][C:4](=[O:6])[NH:5][C:1]2=[O:7])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 10935MaleimideHCID 127654-Methoxybenzenethiol

Product 1

HCID 12988939HCID 12988939, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  1. customafter 18 hours at room temperature the solvent was removed

Sources & evidence

ORD record
ord-10cf1a004b6c48ce9b199d460573d286
Source dataset
uspto-grants-2005_03
Patent number
US06861445B2

Reaction notes

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