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

HRID 1864374Notes

Reaction equation

HRID 1864374 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+].[Cl:33][C:34]1[CH:35]=[CH:36][C:37]([CH3:46])=[C:38]([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH:39]=1>>[Cl:33][C:34]1[CH:35]=[CH:36][C:37]([CH3:46])=[C:38]([N:40]2[CH2:41][CH2:42][N:43]([C:3]([CH:5]3[CH2:7][N:6]([S:8]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=4)(=[O:9])=[O:10])[C:29](=[O:30])[N:28]3[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[Cl:21])=[O:4])[CH2:44][CH2:45]2)[CH:39]=1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 76833Chlorophenyl isocyanateHCID 693767N-(5-Chloro-2-methylphenyl)piperazineHCID 86623479(RS)-1-(3-methoxy-benzenesulfonyl)-aziridine-2-carboxylic acid methyl ester

Product 1

HCID 25027932(RS)-4-[4-(5-Chloro-2-methyl-phenyl)-piperazine-1-carbonyl]-3-(2-chloro-phenyl)-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-(5-chloro-2-methylphenyl)-piperazine gave the title compound as a colorless solid. MS: 603.3 ([M+H]+)

Sources & evidence

ORD record
ord-cc305657cdbb46d19ada057385896392
Source dataset
uspto-grants-2009_12
Patent number
US07625902B2

Reaction notes

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