Iodine → 4-Iodo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1h-benzoimidazole-5-carbonitrile

HRID 1661934Notes

Reaction equation

HRID 1661934 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:25][CH3:26])=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[I:27]I.[OH-].[Na+]>C(O)(=O)C.S([O-])([O-])(=O)=O.[Ag+2]>[I:27][C:22]1[C:12]2[N:11]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=3)[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]=2[C:19]([O:25][CH3:26])=[CH:20][C:21]=1[C:23]#[N:24]

Participants

6

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 112795222-(4-Isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbonitrile

Product 1

HCID 114201314-Iodo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1h-benzoimidazole-5-carbonitrileYield 14.7%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 50 mg (0.143 mmol) 2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbonitrile and 36 mg (0.143 mmol) iodine and 22 mg (0.072 mmol) silver sulfate in 1 ml acetic acid is stirred at reflux for 3 h. Then the filtrate is poured on 2N NaOH and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) to afford 10 mg of the title compound as a white crystalline solid.

Workup

  1. temperatureat reflux for 3 h
  2. extractionextracted (3×) with ethyl acetate
  3. washThe combined organic layers are washed with water (2×) and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1)

Sources & evidence

ORD record
ord-0152a9b46beb4bdc98daef95f1f5fa1b
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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