Acetic Anhydride → 2-Acetylamino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester

HRID 916257Notes

Reaction equation

HRID 916257 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.CCN(CC)CC.[CH3:25][C:26](OC(C)=O)=[O:27]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH:17][C:26](=[O:27])[CH3:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 150541832-Amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester

Product 1

HCID 694926452-Acetylamino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl esterYield 98.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (46.6 mg, 0.20 mmol), Et3N (26.0 mg, 0.26 mmol) and DMAP (2.5 mg, 0.02 mmol) in CH2Cl2 (4 mL) was added dropwise Ac2O (24.5 mg, 0.24 mmol), and the reaction mixture was then heated to reflux under argon for 1 hr. Cooled to r.t., the reaction mixture was concentrated and the residue was partitioned between EtOAc and water. The organic layer was dried over Na2SO4 and concentrated to give 2-acetylamino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester as an oil (54.0 mg, 98.2%).

Workup

  1. temperaturethe reaction mixture was then heated
  2. temperatureto reflux under argon for 1 hr
  3. concentrationthe reaction mixture was concentrated
  4. customthe residue was partitioned between EtOAc and water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3d2fd7eac8cc4af9a4145b9a6929bb71
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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