Benzoyl chloride → 4-Benzoyl-1,3-dihydro-2H-imidazol-2-one

HRID 1995664Notes

Reaction equation

HRID 1995664 reaction equation
[N+](C1C=CC=CC=1)([O-])=O.[NH:10]1[CH:14]=[CH:13][NH:12][C:11]1=[O:15].[Cl-].[Al+3].[Cl-].[Cl-].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:20]([C:14]1[NH:10][C:11](=[O:15])[NH:12][CH:13]=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 7412Benzoyl chlorideHCID 7416NitrobenzeneHCID 222082-HydroxyimidazoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 155675304-Benzoyl-1,3-dihydro-2H-imidazol-2-one

Conditions

Temperature
60 °C

Procedure

To 51 ml of nitrobenzene is added 1.68 g of 1,3-dihydro-2H-imidazol-2-one, 5.3 g of aluminum chloride and 3.1 g of benzoyl chloride. The mixture is stirred for 3 hours at 60° C. and poured into ice water. The solids are filtered, washed with ether and recrystallized twice from methyl alcohol-water to afford the title compound. M.P. 329°-30° C.

Workup

  1. filtrationThe solids are filtered
  2. washwashed with ether
  3. customrecrystallized twice from methyl alcohol-water

Sources & evidence

ORD record
ord-c303f0e93f8d4c1ebf8bd4cec660e988
Source dataset
uspto-grants-1983_09
Patent number
US04405635

Reaction notes

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