Potassium Carbonate → (+/-)-2-Methyl-3-[2-(4-nitro-phenyl)-2-oxo-ethyl]-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one

HRID 507404Notes

Reaction equation

[CH3:1][C:2]1[NH:6][C:5](=[O:7])[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH2:8][CH2:9][CH3:10])[N:3]=1.Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[N:6]([CH2:18][C:19]([C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[O:20])[C:5](=[O:7])[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH2:8][CH2:9][CH3:10])[N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

(+/−)-2-Methyl-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one (541 mg, 2.5 mmol) and 2-bromo-1-(4-nitro-phenyl)-ethanone (707 mg, 2.8 mmol) and potassium carbonate (698 mg, 5 mmol) are dissolved in 5 mL acetone and the reaction mixture is heated at 70° C. for 10 min in the microwave oven (Biotage Initiator). The mixture is cooled to room temperature filtered and the filtrate evaporated. The residue is subjected to flash chromatography (cyclohexane/ethyl acetate-gradient, ethyl acetate 0-100% in 20 min) to yield (+/−)-2-methyl-3-[2-(4-nitro-phenyl)-2-oxo-ethyl]-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one (528 mg, 56%). LC/MS at 254 nm; [M+H] 380; Rt 2.959 min.

Workup

temperatureThe mixture is cooled to room temperature
filtrationfiltered
customthe filtrate evaporated
customis subjected to flash chromatography (cyclohexane/ethyl acetate-gradient, ethyl acetate 0-100% in 20 min)

Sources & evidence

ORD record: ord-9e16d25d0fc24213a4477109acb746cb
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786155B2

Reaction notes

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