Hydrochloric Acid → HCID 22613824, compound

HRID 1533060Notes

Reaction equation

HRID 1533060 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:34]=[CH:33][CH:32]=[CH:31][C:4]=1[C:5]([C:7]1[N:8]([CH2:12][CH:13]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[CH2:14][CH2:15][O:16]C2CCCCO2)[CH:9]=[CH:10][N:11]=1)=[O:6].Cl>CO>[Cl:30][C:25]1[CH:24]=[C:23]([CH:13]([CH2:12][N:8]2[CH:9]=[CH:10][N:11]=[C:7]2[C:5](=[O:6])[C:4]2[CH:31]=[CH:32][CH:33]=[CH:34][C:3]=2[C:2]([F:1])([F:35])[F:36])[CH2:14][CH2:15][OH:16])[CH:28]=[CH:27][C:26]=1[Cl:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22613822HCID 22613822, compound

Product 1

HCID 22613824HCID 22613824, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[2-(2-Trifluoromethylbenzoyl)imidazol-1-yl]-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane (0.68 g) (see Preparation 59) was dissolved in methanol (15 ml), which had been previously saturated with hydrogen chloride gas, and left to stand for 4 hours. The solvent was then removed under reduced pressure to give a residue which was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate solution (the pH of the aqueous layer was kept at 8-9). The organic phase was separated and the aqueous phase extracted (twice) with dichloromethane. The organic phases were then combined, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give 3-(3,4-dichlorophenyl)-4-[2-(2-trifluoromethylbenzoyl)imidazol-1-yl]butan-1-ol (0.41 g) as a white foam.

Workup

  1. waitleft
  2. customThe solvent was then removed under reduced pressure
  3. customto give a residue which
  4. customwas partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate solution (the pH of the aqueous layer
  5. customThe organic phase was separated
  6. extractionthe aqueous phase extracted (twice) with dichloromethane
  7. dry with materialdried over anhydrous sodium sulphate
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b236ca534191411e9495c0f4aaf53450
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

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