Urea → 4-(4-dimethylaminophenyl)-2,3dihydro-5-phenyl-1H-imidazol-2-one

HRID 2135

Reaction equation

HRID 2135 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].[CH3:5][N:6]([CH3:23])[C:7]1[CH:12]=[CH:11][C:10]([CH:13](O)[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=O)=[CH:9][CH:8]=1>C(O)(=O)C>[CH3:23][N:6]([CH3:5])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:1][C:2](=[O:3])[NH:4][C:14]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 5906282-[4-(Dimethylamino)phenyl]-2-hydroxy-1-phenylethanone

Product 1

HCID 540115654-(4-dimethylaminophenyl)-2,3dihydro-5-phenyl-1H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To acetic acid (2 mL) was added urea (0.6 g, 10 mmol) and 2-(4-dimethylaminophenyl)-2-hydroxy-1-phenylethanone (2.6 g, 10 mmol). After stirring for 2 hours at 120° C., the reaction was cooled to ambient temperature. The resulting solid was filtered, washed with ether, and dried in vacuo to give 4-(4-dimethylaminophenyl)-2,3-dihydro-5-phenyl-1H-imidazol-2-one; NMR (CDCl3) 10.98 (s,2), 7.5 (m,4), 7.4 (m,5), 3.18 (s,6) ppm.

Workup

  1. temperaturethe reaction was cooled to ambient temperature
  2. filtrationThe resulting solid was filtered
  3. washwashed with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e289c3d74b254a4196a9c35ea0894330
Source dataset
uspto-grants-1998_03
Patent number
US05728697

Linked notes

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