Ammonium Chloride → HCID 22130053, compound

HRID 1857785Notes

Reaction equation

HRID 1857785 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[N:11]([CH2:27][C:28](=[O:30])[CH3:29])[C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][CH2:9][C:10]1[N:11]([CH2:27][C:28]([OH:30])([CH3:31])[CH3:29])[C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 22130068HCID 22130068, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 22130053HCID 22130053, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 5 ml of tetrahydrofuran was dissolved 464 mg (1 mmol) of the ketone (139), followed by addition dropwise of 134 mg (1.1 mmol) of methylmagnesium bromide (tetrahydrofuran;2 ml) under ice-cooling and stirring, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added an aqueous solution of ammonium chloride, the mixture was distilled off under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off. The residue was purified by silica gel column chromatography (ethyl acetate:methylene chloride=1:1) to provide 350 mg (yield 73%) of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-1-(2-hydroxy-2-methylpropyl)-4-isopropyl-1H-imidazole (140b) as oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. distillationthe mixture was distilled off under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:methylene chloride=1:1)

Sources & evidence

ORD record
ord-d16dd164bfc449cab8817eeaa3079e8e
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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