Ammonium Acetate → HCID 178442428, compound

HRID 1881484Notes

Reaction equation

C([O-])(=O)C.[NH4+:5].[C:6]([NH:9][CH:10]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1)[C:11]([NH:13][CH2:14][C:15](=O)[CH2:16][C:17]([CH3:21])([CH3:20])[CH2:18][CH3:19])=O)(=[O:8])[CH3:7]>C1(C)C(C)=CC=CC=1>[Br:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][CH:10]([NH:9][C:6](=[O:8])[CH3:7])[C:11]2[NH:13][CH:14]=[C:15]([CH2:16][C:17]([CH3:21])([CH3:20])[CH2:18][CH3:19])[N:5]=2)=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Ammonium acetate (1.17 g, 79 mmol) was added to an ambient temperature solution of 2-(acetylamino)-3-(4-bromophenyl)-N-(4,4-dimethyl-2-oxohexyl)propanamide (650 mg, 1.58 mmol) in xylene (10 mL). After stirring at 150° C. for 1 h, the reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate and methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% acetone/methylene chloride afforded N-{2-(4-bromophenyl)-1-[4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}acetamide.

Workup

customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate
extractionextracted with ethyl acetate and methylene chloride
dry with materialThe combined organic extracts were dried (magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-cbf3c9610ca042e19aa3402041031a1e
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318767B2

Reaction notes

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