Potassium Carbonate → 1-(4-trifluoromethylphenyl)imidazolidin-2-one

HRID 2194830Notes

Reaction equation

HRID 2194830 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)=[O:6].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 256324N'-(2-Chloroethyl)-N-[4-(trifluoromethyl)phenyl]carbamimidic acid

Product 1

HCID 106809511-(4-trifluoromethylphenyl)imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-trifluoromethylaniline (3.47 g, 21.6 mmol) in dry toluene (50 mL) was added 2-chloroethylisocyante (2.50 g, 2.02 mL, 23.7 mmol). The mixture was stirred at 40° C. for 12 h. After cooling to room temperature, the solid was collected by filtration and washed with toluene, water and dried in air to provide 1-(2-chloro-ethyl)-3-(4-trifluoromethylphenyl)urea [5.28 g, 92.0%, >95% pure by LC/MS MS (ES+) m/z: 267, 269]. The urea (5.27 g, 23.7 mmol) was then stirred in DMF (50.0 mL) with K2CO3 (3.27 g, 11.98 mmol) at room temperature for 12 h. The solid was filtered off and the solvent was removed in vacuum. The crude product was dissolved in dichloromethane and passed through a silica column (50 g) and eluted with dichloromethane:ethyl acetate, 8:2 to give pure cyclic urea intermediate, 1-(4-trifluoromethylphenyl) imidazolidin-2-one, as white crystalline material (3.85 g, 84.7%). MS (ES+) m/z: 231.

Workup

  1. filtrationThe solid was filtered off
  2. customthe solvent was removed in vacuum
  3. dissolutionThe crude product was dissolved in dichloromethane
  4. washeluted with dichloromethane

Sources & evidence

ORD record
ord-f3f844443dc54177929ccfcacae51cec
Source dataset
uspto-grants-2012_12
Patent number
US08334313B2

Reaction notes

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