Maleimide → HCID 12988939, compound

HRID 498098Notes

Reaction equation

HRID 498098 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 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.

Workup

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

Sources & evidence

ORD record
ord-33e0dac4dcc64f819e59e685e871f2d4
Source dataset
uspto-grants-2005_09
Patent number
US06949661B2

Reaction notes

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