Cesium carbonate → HCID 66603072, compound

HRID 2194829Notes

Reaction equation

HRID 2194829 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=3)[C:16]([OH:18])=[O:17])[C:9]2=[O:22])=[CH:4][CH:3]=1.[NH:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28].[C:29]([O-])([O-])=O.[Cs+].[Cs+].O1CCOCC1>O.[Cu]I>[CH3:29][O:18][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][CH:21]=[C:13]([N:10]2[CH2:11][CH2:12][N:8]([C:5]3[CH:6]=[CH:7][C:2]([N:23]4[CH2:27][CH2:26][CH2:25][C:24]4=[O:28])=[CH:3][CH:4]=3)[C:9]2=[O:22])[CH:14]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 312751,4-DioxaneHCID 104315563-[3-(4-iodophenyl)-2-oxo-imidazolidin-1-yl]benzoic Acid

Product 1

HCID 66603072HCID 66603072, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

The methyl ester of 3-[3-(4-iodophenyl)-2-oxo-imidazolidin-1-yl]benzoic acid (0.42 g, 1.0 mmol) prepared as in Example 13 was mixed with 2-pyrrolidinone (0.10 g, 0.09 mL, 1.2 mmol), CuI (0.02 g, 0.10 mmol), Cs2CO3 (0.65 g, 2.0 mmol), trans-1,2-hexanediamine (0.01 g, 0.01 mL, 0.1 mmol) and dioxane (5 mL). The mixture was heated at 110° C. with stirring for 12 h under nitrogen. After cooling to room temperature, the mixture was diluted with water (10 mL) and extracted with dichloromethane (10 mL×3) and the combined extracts were washed with water, brine and dried over anhydrous Na2SO4, and then concentrated. The crude product obtained after the removal of the solvent was chromatographed (silica, dichloromethane: ethyl acetate, 9:1) to provide pure product, 3-{2-oxo-3-[4-(2-oxo-pyrrolidin-1-yl)phenyl]imidazolidin-1-yl}benzoic acid methyl ester, as white solid (0.34 g, 89.5%). MS (ES+) m/z: 380.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with dichloromethane (10 mL×3)
  3. washthe combined extracts were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe crude product obtained
  7. customafter the removal of the solvent
  8. customwas chromatographed (silica, dichloromethane: ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-00964ed6cae343daad0344e754cba60a
Source dataset
uspto-grants-2012_12
Patent number
US08334313B2

Reaction notes

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