Nitrobenzene → 4-Nitrobenzoyl-1,3-dihydroimidazol-2-one

HRID 1348951Notes

Reaction equation

HRID 1348951 reaction equation
[NH:1]1[CH:5]=[CH:4][NH:3][C:2]1=[O:6].[N+](C1C=CC=CC=1[C:12](Cl)=[O:13])([O-])=O.[N+:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([O-:21])=[O:20]>[Al+3].[Cl-].[Cl-].[Cl-]>[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([C:12]([N:1]2[CH:5]=[CH:4][NH:3][C:2]2=[O:6])=[O:13])=[CH:24][CH:23]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 7416NitrobenzeneHCID 118752-Nitrobenzoyl chlorideHCID 222082-Hydroxyimidazole

Product 1

HCID 210928284-Nitrobenzoyl-1,3-dihydroimidazol-2-oneYield 45%

Reagents, catalysts & solvents 1

HCID 6451240Aluminum(III) ChlorideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of dihydroimidazolone 1a (1.0 g, 11.9 mmol) in 24 mL 1M AlCl3 in nitrobenzene was added 2-nitrobenzoyl chloride (2.2 g, 11.9 mmol), and the reaction was heated in a 65° C. oil bath for 6 h. The reaction was poured over ice during which a solid formed. The reaction was filtered through a sintered glass funnel and the solid washed with water and diethyl ether and dried in vacuum dessicator to give 1.26 g (45% yield) of 4-nitrobenzoyl-1,3-dihydroimidazol-2-one 1b.

Workup

  1. additionThe reaction was poured over ice during which a solid
  2. customformed
  3. filtrationThe reaction was filtered through a sintered glass funnel
  4. washthe solid washed with water and diethyl ether
  5. customdried in vacuum dessicator

Sources & evidence

ORD record
ord-b2223c12bb7f4474bfe3be473641f456
Source dataset
uspto-grants-2007_05
Patent number
US07211671B2

Reaction notes

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