Ammonium Acetate → HCID 178442428, compound

HRID 425402Notes

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: 15 °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 15° 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-805becbb24354debac61bbee4269acb7
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106070B2

Reaction notes

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