Potassium Carbonate → 4-[2-(2-Methyl-5-oxo-4,4-diphenyl4,5-dihydro-imidazol-1-yl)-acetyl]-benzoic acid ethyl ester

HRID 507398

Reaction equation

[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12]Br)=[CH:7][CH:6]=1)[CH3:2].[CH3:16][C:17]1[NH:21][C:20](=[O:22])[C:19]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=1.C(=O)([O-])[O-].[K+].[K+].C1CCCCC1.C(OCC)(=O)C>CC(C)=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12][N:21]2[C:20](=[O:22])[C:19]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:18]=[C:17]2[CH3:16])=[CH:7][CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 4-(2-bromo-acetyl)-benzoic acid ethyl ester (812 mg, 3 mmol) and 2-methyl-5,5-diphenyl-3,5-dihydro-imidazol-4-one (750 mg, 3 mmol) in 12 mL acetone, potassium carbonate (502 mg, 3.6 mmol) is added and the reaction mixture is heated at 70° C. for 5 min in the microwave oven (Biotage Initiator). The mixture is cooled to room temperature, filtered and the filtrate evaporated to yield the crude product which is subjected to flash chromatography. ISCO Companion CombiFlash, 80 g silica gel, cyclohexane/ethyl acetate, gradient, ethyl acetate 0-100% to yield 4-[2-(2-methyl-5-oxo-4,4-diphenyl4,5-dihydro-imidazol-1-yl)-acetyl]-benzoic acid ethyl ester (635 mg, 45%) as light yellow solid. LC/MS at 254 nm; [M+H] 441; Rt 3.613 min.

Workup

additionis added
temperatureThe mixture is cooled to room temperature
filtrationfiltered
customthe filtrate evaporated
customto yield the crude product which

Sources & evidence

ORD record: ord-f9d8a6508a3d42dbae724ee41ebb2115
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786155B2

Linked notes

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