Potassium Carbonate → benzyl 5-oxo-2-[[2-(trifluoromethyl)phenyl]methylamino]-4H-imidazole-3-carboxylate

HRID 916263Notes

Reaction equation

HRID 916263 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]([F:29])([F:28])[C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH:17][CH2:22][C:21]1[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=1[C:19]([F:18])([F:28])[F:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 150541832-Amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester

Product 1

HCID 178516790benzyl 5-oxo-2-[[2-(trifluoromethyl)phenyl]methylamino]-4H-imidazole-3-carboxylateYield 48.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (93.2 mg, 0.40 mmol), 2-trifluoromethyl-benzylbromide (95.6 mg, 0.40 mmol) and K2CO3 (83.01 mg, 0.60 mmol) in acetonitrile (10 mL) was heated to reflux under argon for 1 hr. Cooled to r.t. and the reaction mixture was partitioned between EtOAc and water. The organic layer was dried over Na2SO4 and concentrated to give a residue which was triturated with EtOAc and filtered to give 4-oxo-2-(2-trifluoromethyl-benzylamino)-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester as a white solid (75.0 mg, 48.1%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon for 1 hr
  3. customthe reaction mixture was partitioned between EtOAc and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto give a residue which
  7. customwas triturated with EtOAc
  8. filtrationfiltered

Sources & evidence

ORD record
ord-62b71475acfa447d9fbcd512485b8514
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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