Sodium Iodide → (RS)-1-(3-methoxy-benzenesulfonyl)-2-oxo-3-phenyl-imidazolidine-4-carboxylic acid methyl ester

HRID 1864361Notes

Reaction equation

HRID 1864361 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:7][N:6]1[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)(=[O:10])=[O:9])=[O:4].[I-].[Na+].[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:7][N:6]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)(=[O:9])=[O:10])[C:28](=[O:29])[N:27]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:4]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 7672Phenyl isocyanateHCID 86623479(RS)-1-(3-methoxy-benzenesulfonyl)-aziridine-2-carboxylic acid methyl ester

Product 1

HCID 67141140(RS)-1-(3-methoxy-benzenesulfonyl)-2-oxo-3-phenyl-imidazolidine-4-carboxylic acid methyl esterYield 42.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (RS)-1-(3-methoxy-benzenesulfonyl)-aziridine-2-carboxylic acid methyl ester (0.098 g) in tetrahydrofuran (3 ml) were added sodium iodide (0.054 g) and phenylisocyanate (0.043 g). The mixture was stirred for 18 h at room temperature. The mixture was diluted with ethyl acetate and washed with water, 1% aqueous Na2S2O3 solution and again with water. The organic phase was dried, filtered and evaporated. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 9:1=>1:1) to give (RS)-1-(3-methoxy-benzenesulfonyl)-2-oxo-3-phenyl-imidazolidine-4-carboxylic acid methyl ester (0.060 g) as a colorless solid. MS: 391.1 ([M+H]+)

Workup

  1. washwashed with water, 1% aqueous Na2S2O3 solution and again with water
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 9:1=>1:1)

Sources & evidence

ORD record
ord-0c985af53c6b43d2820667d66548e84e
Source dataset
uspto-grants-2009_12
Patent number
US07625902B2

Reaction notes

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