Sodium Iodide → 1-Benzenesulfonyl-4-(4-bromo-phenyl)-3-phenyl-imidazolidin-2-one

HRID 560083Notes

Reaction equation

HRID 560083 reaction equation
[C:1]1([S:7]([N:10]2[CH2:12][CH:11]2[C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-].[Na+].[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1.C(OCC)(=O)C>[C:1]1([S:7]([N:10]2[CH2:12][CH:11]([C:13]3[CH:14]=[CH:15][C:16]([Br:19])=[CH:17][CH:18]=3)[N:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:29]2=[O:30])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 7672Phenyl isocyanateHCID 468456691-Benzenesulfonyl-2-(4-bromo-phenyl)-aziridine

Product 1

HCID 670012201-Benzenesulfonyl-4-(4-bromo-phenyl)-3-phenyl-imidazolidin-2-oneYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-benzenesulfonyl-2-(4-bromo-phenyl)-aziridine (1.00 g) in tetrahydrofuran (16.5 mL) under argon were added sodium iodide (0.487 g) and phenylisocyanate (0.539 g). The mixture was stirred for 5 days at room temperature. The mixture was diluted with ethyl acetate (50 mL) and washed with water. The org. phase was dried (MgSO4), filtered and concentrated. The product was purified using column chromatography (SiO2, cyclohexane/ethyl acetate 1:0=>0:1) to give 1-benzenesulfonyl-4-(4-bromo-phenyl)-3-phenyl-imidazolidin-2-one (0.974 g) as a colorless solid. MS: 458.9 ([M+H]+)

Workup

  1. washwashed with water
  2. dry with materialphase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified

Sources & evidence

ORD record
ord-87b6bd17fbc642c88b73af3367a325d7
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

Loading…