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

HRID 370549Notes

Reaction equation

HRID 370549 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-one

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 moles) of anhydrous aluminum chloride and 500 ml of nitrobenzene there 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 onto 2 kg of ice. The precipitate which forms is separated by filtration, washed with diethyl ether and water and recrystallized from dimethylformamide to give 1,3-dihydro-4-(4-fluorobenzoyl)-5-methyl-2H-imidazol-2-one melting at about 289°-292° C.

Workup

  1. additionthere is added dropwise over 10 minutes
  2. customThe precipitate which forms is separated by filtration
  3. washwashed with diethyl ether and water
  4. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-8fc6f66a1ee54ceeb09961ad8fc596b9
Source dataset
uspto-grants-1985_07
Patent number
US04526981

Reaction notes

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