Ammonium Chloride → HCID 178488535, compound

HRID 1059141Notes

Reaction equation

HRID 1059141 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([C:8]2[CH:9]=[C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:11]=[CH:12][C:13]=2[O:14][CH3:15])=[O:7])[N:3]=[CH:2]1.[CH:22]([Mg]Cl)([CH3:24])[CH3:23].[Cl-].[NH4+]>C1COCC1.O>[NH:1]1[CH:5]=[C:4]([C:6]([C:8]2[CH:9]=[C:10]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:11]=[CH:12][C:13]=2[O:14][CH3:15])([OH:7])[CH:22]([CH3:24])[CH3:23])[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 178418918HCID 178418918, compoundHCID 178488533HCID 178488533, compound

Product 1

HCID 178488535HCID 178488535, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

1H-Imidazol-4-yl(4-methoxy[1,1′-biphenyl]-3-yl)methanone (0.62 g) was dissolved in THF (15 ml) and the mixture was cooled to −40° C. A solution (0.6 M; 15 ml) of isopropyl magnesium chloride in THF was slowly added dropwise and the mixture was warmed to room temperature. The mixture was stirred for 1 h and thereto was added saturated aqueous ammonium chloride solution. The mixture was diluted with water and extracted with ethyl acetate. The extract was dried and concentrated. The obtained residue was purified by silica gel column chomatography (eluent, dichloromethane:methanol=40:1) to give the colorless amorphous title compound (0.16 g).

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. extractionextracted with ethyl acetate
  3. customThe extract was dried
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chomatography (eluent, dichloromethane:methanol=40:1)

Sources & evidence

ORD record
ord-1fd182301bdd4590b635f20cae3d47ad
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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