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

HRID 370549

Reaktionsgleichung

Reaktionsgleichung von HRID 370549
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7416NitrobenzeneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8fc6f66a1ee54ceeb09961ad8fc596b9
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04526981

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