Ammonium Chloride → HCID 178488534, compound

HRID 1059139Notes

Reaction equation

Br[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.C([Li])(C)(C)C.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][C:15]=1[CH:26]=[O:27].[Cl-].[NH4+]>C1COCC1.CCCCC>[NH:5]1[CH:6]=[C:2]([CH:26]([C:15]2[CH:16]=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:18]=[CH:19][C:14]=2[O:13][CH3:12])[OH:27])[N:3]=[CH:4]1

Participants

Conditions

Temperature: -78 °C

Procedure

4-Bromo-1H-imidazole (5.20 g) was dissolved in THF (50 ml) and the mixture was cooled to −78° C. A solution (1.7 M; 50 ml) of t-butyllithium in pentane was added. The mixture was stirred at 0° C. for 1.5 h and cooled to −78° C. again. A solution (30 ml) of 4-methoxy[1,1′-biphenyl]-3-carbaldehyde (2.54 g) in THF was added, and the mixture was heated from −78° C. to room temperature and further stirred at room temperature for 24 h. Aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried and concentrated. The residue was purified by silica gel column chomatography (eluent, dichloromethane:methanol=15:1) and recrystallized from ethyl acetate to give the title compound (1.15 g) as a colorless solid.

Workup

temperaturecooled to −78° C. again
temperaturethe mixture was heated from −78° C. to room temperature
stirringfurther stirred at room temperature for 24 h
extractionthe mixture was extracted with ethyl acetate
customThe organic layer was dried
concentrationconcentrated
customThe residue was purified by silica gel column chomatography (eluent, dichloromethane:methanol=15:1)
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-65a646e8874844b48093ebae130913d2
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518257B1

Reaction notes

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