Ammonium Acetate → HCID 178488783, compound

HRID 599640Notes

Reaction equation

HRID 599640 reaction equation
C([O-])(=O)C.[NH4+:5].[CH3:6][O:7][C:8]1[CH:9]=[C:10](/[CH:20]=[CH:21]/[C:22]([NH:24][CH2:25][C:26]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=O)=O)[CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1>C(O)(=O)C>[CH3:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([C:26]2[N:5]=[C:22](/[CH:21]=[CH:20]/[C:10]3[CH:11]=[CH:12][C:13]([N:14]4[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]4)=[C:8]([O:7][CH3:6])[CH:9]=3)[NH:24][CH:25]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 67067186(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-[2-(4-methoxyphenyl)-2-oxoethyl]acrylamide

Product 1

HCID 178488783HCID 178488783, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

Ammonium acetate (379 mg) was added to a solution of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-[2-(4-methoxyphenyl)-2-oxoethyl]acrylamide (100 mg) in acetic acid (3 mL), and the reaction solution was stirred at 120° C. for 12 hours. The reaction solution was concentrated. Ethyl acetate and saturated sodium bicarbonate water were added to the resulting residue, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate:2-propanol=20:1) to obtain 15 mg of the title compound. The property values of the compound are as follows.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionEthyl acetate and saturated sodium bicarbonate water were added to the resulting residue
  3. customthe organic layer was separated
  4. washThe resulting organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate:2-propanol=20:1)

Sources & evidence

ORD record
ord-6d0d269030a54c97b8606904a449d230
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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