Ammonium Chloride → HCID 178488575, compound

HRID 1059134Notes

Reaction equation

HRID 1059134 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.[NH:21]1[CH:25]=[C:24]([C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])[N:23]=[CH:22]1.[Cl-].[NH4+]>C1COCC1.CCCCCC>[NH:21]1[CH:25]=[C:24]([C:26]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)([OH:30])[CH:27]([CH3:29])[CH3:28])[N:23]=[CH:22]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 40340054-Bromo-4'-methoxybiphenylHCID 178418339ButyllithiumHCID 178450295HCID 178450295, compound

Product 1

HCID 178488575HCID 178488575, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

4-Bromo-4′-methoxy-1,1′-biphenyl (1.95 g) was dissolved in THF (40 ml) and the mixture was cooled to −78° C. A solution (1.6 M; 5.5 ml) of n-butyllithium in hexane was added dropwise, and the mixture was stirred at −78° C. for 1 h. Then, a solution (10 ml) of 1-(1H-imidazol-4-yl)-2-methyl-1-propanone (335 mg) in THF was slowly added dropwise. The reaction mixture was heated from −78° C. to room temperature and saturated aqueous ammonium chloride solution was added to the reaction mixture. The mixture was extracted with ethyl acetate and the organic layer was dried and concentrated. The obtained residue was recrystallized from ethyl acetate to give the title compound (322 mg) as a colorless solid.

Workup

  1. temperatureThe reaction mixture was heated from −78° C. to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe organic layer was dried
  4. concentrationconcentrated
  5. customThe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-85164d6553684c5fa2859280b693ed18
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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