Imidazole → [3-(1H-Imidazol-1-yl)phenyl](2,4,6-trimethylphenyl)methanone

HRID 1380300Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.F[C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[C:12]([C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=1[CH3:22])=[O:13]>CN(C)P(=O)(N(C)C)N(C)C>[N:3]1([C:9]2[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=2)[C:12]([C:14]2[C:15]([CH3:22])=[CH:16][C:17]([CH3:21])=[CH:18][C:19]=2[CH3:20])=[O:13])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a suspension of 2.9 g of sodium hydride (60% dispersion in mineral oil) in 50 ml of hexamethylphosphoric triamide is added 5.3 g of imidazole over a 30 minute period under heating at 40° C. After the addition is complete, the mixture is stirred at room temperature for an hour. To the reaction mixture is added 16.6 g of 3-fluoro-2',4',6'-trimethylbenzophenone and the mixture is stirred at 70° C. for 24 hours. The reaction solution is poured into ice-cold water and extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried and concentrated. The residue is recrystallized from a mixture of toluene and isopropyl ether to give 16 g of 3-(1-imidazolyl)-2',4',6'-trimethylbenzophenone as white crystals, melting at 134°-136° C.

Workup

additionAfter the addition
stirringthe mixture is stirred at 70° C. for 24 hours
additionThe reaction solution is poured into ice-cold water
extractionextracted with ethyl acetate
washThe ethyl acetate layer is washed with water
customdried
concentrationconcentrated
customThe residue is recrystallized from a mixture of toluene and isopropyl ether

Sources & evidence

ORD record: ord-f4bf90626fa74498b55225cb5a9c8dc3
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04581369

Reaction notes

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