Trifluoroacetic acid → HCID 117759849, compound

HRID 1049558Notes

Reaction equation

HRID 1049558 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23]CC2C=CC(OC)=CC=2)=[CH:19][C:18]=1[C:33]1[S:34][C:35]([C:38]([F:41])([F:40])[F:39])=[N:36][N:37]=1.C1(OC)C=CC=CC=1>>[F:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=1[C:33]1[S:34][C:35]([C:38]([F:39])([F:40])[F:41])=[N:36][N:37]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 117759748HCID 117759748, compound

Product 1

HCID 117759849HCID 117759849, compoundYield 88.6%

Procedure

Trifluoroacetic acid (5.0 mL) was added to 2-(2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)-[1,1′-biphenyl]-2-yl)-5-(trifluoromethyl)-1,3,4-thiadiazole (299 mg) and anisole (0.66 mL) at room temperature, and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was concentrated under reduced pressure, aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (200 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, aqueous sodium hydrogen carbonate solution
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-899f8369b8014071bc39b412bc9aa18d
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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