Ammonium Hydroxide → HCID 178442427, compound

HRID 1927650Notes

Reaction equation

HRID 1927650 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:12][CH2:13][C:14](=O)[CH2:15][C:16]([CH3:20])([CH3:19])[CH2:17][CH3:18])=O)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:26].[OH-].[NH4+]>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[NH:12][CH:13]=[C:14]([CH2:15][C:16]([CH3:20])([CH3:19])[CH2:17][CH3:18])[N:26]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 68673705HCID 68673705, compound

Product 1

HCID 178442427HCID 178442427, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 3-(4-bromophenyl)-N-(4,4-dimethyl-2-oxohexyl)propionamide (71.5 g, 202 mmol), ammonium acetate (770 g, 10 mol) and acetic acid (700 mL) was heated at 160° C. for 20 h. Upon cooling, the reaction mixture was poured onto ice (600 mL), and the pH was adjusted to ˜10 with concentrated ammonium hydroxide. The product was extracted with ethyl acetate, and the extracts were dried over sodium sulfate and concentrated to provide 2-[2-(4-bromophenyl)ethyl]-4-(2,2-dimethylbutyl)-1H-imidazole, which was used without purification.

Workup

  1. temperatureUpon cooling
  2. additionthe reaction mixture was poured onto ice (600 mL)
  3. extractionThe product was extracted with ethyl acetate
  4. dry with materialthe extracts were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-debf94f122e04b569dd605a72001fca9
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

Loading…