Iodine → HCID 57719296, compound

HRID 1985120Notes

Reaction equation

HRID 1985120 reaction equation
[C:1]([C:5]1[CH:29]=[CH:28][C:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[N:12]([CH3:26])[C:11]2=[O:27])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[I:30]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[C:1]([C:5]1[CH:29]=[CH:28][C:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[C:22]([I:30])[CH:23]=3)[N:12]([CH3:26])[C:11]2=[O:27])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 807IodineHCID 68869690HCID 68869690, compound

Product 1

HCID 57719296HCID 57719296, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(4-tert-Butyl-benzyl)-4-[3-(4-methoxy-phenyl)-propyl]-3-methyl-imidazolidin-2-one (0.630 g, 1.60 mmole) in ethanol (15 mL), is added iodine (0.810 g, 3.20 mmole) followed by silver sulfate (0.998 g, 3.20 mmole). The reaction mixture is stirred at room temperature overnight. The precipitate is removed through filtration, and the solution is concentrated in vacuo. The residue is purified by column chromatography (silica gel, gradient elution 0-20% acetone in hexane) to provide a white foamy solid (0.584 g, 70%). Mass [EI+] 521 (M+H)+.

Workup

  1. customThe precipitate is removed through filtration
  2. concentrationthe solution is concentrated in vacuo
  3. customThe residue is purified by column chromatography (silica gel, gradient elution 0-20% acetone in hexane)

Sources & evidence

ORD record
ord-44097d66e42246249a5c703b9c79e968
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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