Ammonium Chloride → HCID 66608944, compound

HRID 71155Notes

Reaction equation

HRID 71155 reaction equation
[CH3:1][Mg]Br.[Cl:4][C:5]1[CH:6]=[C:7]([C:12](=[O:32])[CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[N:27][C:26]([CH3:29])=[N:25]3)=[C:20]([O:30][CH3:31])[CH:19]=2)[CH:8]=[CH:9][C:10]=1[Cl:11].[Cl-].[NH4+]>C1COCC1>[Cl:4][C:5]1[CH:6]=[C:7]([C:12]([OH:32])([CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[N:27][C:26]([CH3:29])=[N:25]3)=[C:20]([O:30][CH3:31])[CH:19]=2)[CH3:1])[CH:8]=[CH:9][C:10]=1[Cl:11]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 666084331-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-oneHCID 178418573HCID 178418573, compound2×

Product 1

HCID 66608944HCID 66608944, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (12% THF solution, 550 μL) was added to a mixture of 1-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-one (198 mg) in THF (5 mL) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Methylmagnesium bromide (12% THF solution, 550 μL) was added to the reaction mixture under ice-cooling, and the mixture was stirred for 15 min under ice-cooling. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (177 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 15 min under ice-
  4. temperaturecooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8018944572554ad0a06e2674e2513dce
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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