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

HRID 2723

Reaction equation

HRID 2723 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)-2,3dihydro-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-4eef7a1f326e44c69373eeaaece2675b
Source dataset
uspto-grants-1998_03
Patent number
US05731311

Linked notes

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