4-Fluorobenzoyl chloride → 4-(4-Fluorobenzoyl)-5-methyl-1,3-dihydro-2H-imidazol-2-one

HRID 1995654Notes

Reaction equation

HRID 1995654 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:7])[NH:5][CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-].[F:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1>[N+](C1C=CC=CC=1)([O-])=O>[F:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([C:6]2[NH:5][C:4](=[O:7])[NH:3][C:2]=2[CH3:1])=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 709351,3-dihydro-4-methyl-2H-imidazol-2-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 155675394-(4-Fluorobenzoyl)-5-methyl-1,3-dihydro-2H-imidazol-2-oneYield 59.5%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

To a stirred mixture of 98.1 g (1 mole) of 1,3-dihydro-4-methyl-2H-imidazol-2-one, 266.7 g (2 mole) of anhydrous aluminum chloride and 500 ml of nitrobenzene is added dropwise over 10 minutes, 158.6 g (1 mole) of p-fluorobenzoyl chloride. The mixture is stirred at 60°-65° C. for 6 hours, then poured on 2 kg of ice. The resulting precipitate is washed with diethyl ether and water and is recrystallized from 1.2 liters of dimethylformamide to give 131 g of the title compound. M.P. 289°-292° C.

Workup

  1. additionis added dropwise over 10 minutes
  2. washThe resulting precipitate is washed with diethyl ether and water
  3. customis recrystallized from 1.2 liters of dimethylformamide

Sources & evidence

ORD record
ord-6c6ef97f37114fff96f38070c3a5aee0
Source dataset
uspto-grants-1983_09
Patent number
US04405635

Reaction notes

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