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

HRID 916269

Reaction equation

HRID 916269 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.[CH3:18][C:19]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:20]=1[CH2:21]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][CH2:21][C:20]1[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:19]=1[CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27346041-(Bromomethyl)-2,4-dimethylbenzeneHCID 150541832-Amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester

Product 1

HCID 178425527benzyl 2-[(2,4-dimethylphenyl)methylamino]-5-oxo-4H-imidazole-3-carboxylateYield 24.9%

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), 2,4-dimethylbenzylbromide (79.64 mg, 0.40 mmol) and K2CO3 (83.01 mg, 0.60 mmol) in acetonitrile (8 mL) was heated to reflux under argon for 45 min. Partition between EtOAc and water to give a suspension. Filter off the solid to give 2-(2,4-dimethyl-benzylamino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (35.0 mg). The filtrate was separated, dried to give an oil which was purified by preparative TLC, eluted with 50% nHex/EtOAc to give 60.0 mg of 2-(2, 4-dimethyl-benzylamino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester as a white solid (total yield: 95.0 mg, 67.7%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon for 45 min
  3. customPartition between EtOAc and water
  4. customto give a suspension
  5. filtrationFilter off the solid

Sources & evidence

ORD record
ord-5f26461ea2034018b59668be95f02de0
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Linked notes

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