Methyl iodide → 4-[2,5-Dioxo-4-hydroxymethyl-3-methyl-4-phenylimidazolidin-1-yl]-2-methoxybenzonitrile

HRID 2427167Notes

Reaction equation

HRID 2427167 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[O:9]=[C:10]1[NH:14][C:13]([CH2:21][OH:22])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12](=[O:23])[N:11]1[C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([O:32][CH3:33])[CH:25]=1>CN(C=O)C>[O:9]=[C:10]1[N:14]([CH3:1])[C:13]([CH2:21][OH:22])([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:12](=[O:23])[N:11]1[C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([O:32][CH3:33])[CH:25]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 671311834-[2,5-Dioxo-4-hydroxymethyl-4-phenylimidazolidin-1-yl]-2-methoxybenzonitrile

Product 1

HCID 593171894-[2,5-Dioxo-4-hydroxymethyl-3-methyl-4-phenylimidazolidin-1-yl]-2-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

173 mg potassium carbonate and 86 μL methyl iodide are added to a solution of 141 mg 4-[2,5-dioxo-4-hydroxymethyl-4-phenylimidazolidin-1-yl]-2-methoxybenzonitrile in 2 mL DMF. The mixture is stirred overnight at room temperature, evaporated to dryness, The residue is taken in water and extracted with ethyl acetate. The organic layer is dried over magnesium sulfate, filtered, evaporated and chromatographed over silica gel while eluting with 70/30 heptane/ethyl acetate mixture to give the expected product.

Workup

  1. customevaporated to dryness
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customchromatographed over silica gel
  7. washwhile eluting with 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-40316d1bb5b24f1799aa675f8c6334b5
Source dataset
uspto-grants-2011_06
Patent number
US07968581B2

Reaction notes

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