Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → 4-[5-(3,5-Dichloro-phenyl)-2,5-dimethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzamide

HRID 405698Notes

Reaction equation

HRID 405698 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24](F)(F)F)[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.F[B-](F)(F)F.[CH3:33][O+](C)C>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH3:24])[O:13][N:12]([CH3:33])[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[C:16]([CH3:23])[CH:15]=3)=[CH:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)3×HCID 667845734-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide

Product 1

HCID 892620034-[5-(3,5-Dichloro-phenyl)-2,5-dimethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzamideYield 29.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzamide (200 mg) in 1,2-dichloroethane (3 ml) was added trimethyloxonium tetrafluoroborate (85 mg) and the reaction mixture was stirred at room temperature for 19 hours then more trimethyloxonium tetrafluoroborate (210 mg). After 4 hours 30 minutes, more trimethyloxonium tetrafluoroborate (0.5 ml) was added and after 2 hours, the reaction mixture was heated at (85° C.) for 18 hours. The solution was then concentrated under vacuo to give a crude residue (210 mg). Part of this residue (100 mg) of the crude was extracted between AcOEt and saturated NaHCO3. The organic phases were gathered, dried over anhydrous MgSO4, filtered and evaporated to give the desired compound (54 mg). 1H-NMR (CDCl3, δ in ppm): 7.50-7.31 (m, 6H), 5.75 (bs, 2H), 5.41 (s, 1H), 2.99 (s, 3H), 2.52 (s, 3H).

Workup

  1. temperaturethe reaction mixture was heated at (85° C.) for 18 hours
  2. concentrationThe solution was then concentrated under vacuo
  3. customto give a crude residue (210 mg)
  4. extractionPart of this residue (100 mg) of the crude was extracted between AcOEt and saturated NaHCO3
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-b7ac525a66e94810aea5a48371e3663e
Source dataset
uspto-grants-2014_06
Patent number
US08754053B2

Reaction notes

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