Potassium Carbonate → benzyl 2-[(2-chlorophenyl)methylamino]-5-methylidene-4H-imidazole-3-carboxylate

HRID 916254Notes

Reaction equation

HRID 916254 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=O)[N:13]=[C:12]1[NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Br.[C:27]([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[CH2:27])[N:13]=[C:12]1[NH:17][CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=1[Cl:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11905alpha-Bromo-o-chlorotolueneHCID 150541832-Amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester

Product 1

HCID 178430741benzyl 2-[(2-chlorophenyl)methylamino]-5-methylidene-4H-imidazole-3-carboxylateYield 88.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester* (46.62 mg, 0.20 mmol), 2-chlorobenzylbromide (41.0 mg, 0.20 mmol) and K2CO3 (41.4 mg, 0.30 mmol) in acetonitrile (1.5 mL) was heated to reflux under argon for 3 hrs. 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 2-(2-chloro-benzylamino)-4-methylene-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester as an oil (63.0 mg, 88.2%). * 2-amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester was prepared according to the method described by C-H Kwon et al. J. Med. Chem. 1991, 34,1845-1849.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon for 3 hrs
  3. customthe reaction mixture was partitioned between EtOAc and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9cbd98cfd6c44c43addc7e310e9ba53c
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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