Methyl iodide → 3-[4-(4-Chloro-phenoxy)-phenyl]-1-methyl-4-(3-trifluoromethyl-phenyl)-imidazolidin-2-one

HRID 1972193Notes

Reaction equation

HRID 1972193 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[CH2:16][NH:15][C:14]3=[O:28])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:33]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:25])[F:27])[CH:19]=4)[CH2:16][N:15]([CH3:33])[C:14]3=[O:28])=[CH:11][CH:12]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 594856551-(4-(4-Chlorophenoxy)phenyl)-5-(3-(trifluoromethyl)phenyl)imidazolidin-2-one

Product 1

HCID 594858933-[4-(4-Chloro-phenoxy)-phenyl]-1-methyl-4-(3-trifluoromethyl-phenyl)-imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[4-(4-chloro-phenoxy)-phenyl]-5-(3-trifluoromethyl-phenyl)-imidazolidin-2-one (20.0 mg, 0.046 mmol) in anhydrous DMF (0.5 mL) is added NaH (2.2 mg, 60% dispersion in mineral oil, 0.055 mmol) at 0° C. The reaction mixture is stirred at room temperature for 30 minutes before MeI (8.63 μL, 0.138 mmol) is added. The mixture is stirred at room temperature for 2 hours and then partitioned between water and ethyl acetate. The organic layer is concentrated and purified by preparative LC/MC to provide the title compound; HPLC-MS calculated for C23H18ClF3N2O2 (M+H+) 447.1, found 447.1.

Workup

  1. additionis added
  2. custompartitioned between water and ethyl acetate
  3. concentrationThe organic layer is concentrated
  4. custompurified by preparative LC/MC

Sources & evidence

ORD record
ord-e6986c1c0ccf4e0e8b3b78a72c244737
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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