Sodium Iodide → (RS)-3-(2-Chloro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-1-(3-methoxy-benzenesulfonyl)-imidazolidin-2-one

HRID 1864373Notes

Reaction equation

HRID 1864373 reaction equation
CO[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+].[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]=[C:29]=[O:30].[OH-].[Na+].[CH3:33][C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][C:35]=1[N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH:5]([C:3]([N:44]2[CH2:45][CH2:46][N:41]([C:35]3[CH:36]=[C:37]([CH3:40])[CH:38]=[CH:39][C:34]=3[CH3:33])[CH2:42][CH2:43]2)=[O:4])[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:29]1=[O:30]

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 705421-(2,5-Xylyl)piperazineHCID 76833Chlorophenyl isocyanateHCID 86623479(RS)-1-(3-methoxy-benzenesulfonyl)-aziridine-2-carboxylic acid methyl ester

Product 1

HCID 25027931(RS)-3-(2-Chloro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-1-(3-methoxy-benzenesulfonyl)-imidazolidin-2-one

Procedure

In analogy to example 1, (RS)-1-(3-methoxy-benzenesulfonyl)-aziridine-2-carboxylic acid methyl ester (step 2 of example 1) was first reacted with sodium iodide and 2-chlorophenylisocyanate; subsequent ester hydrolysis using sodium hydroxide and coupling with 1-(2,5-dimethylphenyl)-piperazine gave the title compound as a colorless solid. MS: 583.3 ([M+H]+)

Sources & evidence

ORD record
ord-258f8802a95d40cc8884c7bb3f0eb6c7
Source dataset
uspto-grants-2009_12
Patent number
US07625902B2

Reaction notes

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