p-Toluenesulfonic acid → HCID 59644555, compound

HRID 2252001Notes

Reaction equation

HRID 2252001 reaction equation
[F:1][C:2]([F:46])([F:45])[C:3]1[CH:4]=[C:5]([CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]2[O:22][N:21]=[C:20]([CH2:23][CH:24](OC)[O:25]C)[C:19]=2[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[Cl:37])=[O:30])[N:9]=[N:8]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[F:45][C:2]([F:1])([F:46])[C:3]1[CH:4]=[C:5]([CH:38]=[C:39]([C:41]([F:44])([F:42])[F:43])[CH:40]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([C:18]2[O:22][N:21]=[C:20]([CH2:23][CH:24]=[O:25])[C:19]=2[C:29](=[O:30])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[Cl:37])[N:9]=[N:8]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86601218HCID 86601218, compound

Product 1

HCID 59644555HCID 59644555, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

Combine [5-[1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-3-(2,2-dimethoxy-ethyl)-isoxazol-4-yl]-(2-chloro-phenyl)-methanone (1 eq) in acetone/H2O (4:1) and p-toluenesulfonic acid (1 eq) with stirring. Attach a reflux condensor and stir overnight in a 60° C. oil bath. Neutralize with saturated aqueous NaHCO3, extract with ethyl acetate, dry over MgSO4, filter, and concentrate under vacuum. 1H NMR (CDCl3): δ 9.84 (s, 1H), 7.83 (s, 1H), 7.56-7.09 (m, 11H), 5.43 (s, 2H), 4.09 (s, 2H).

Workup

  1. extractionNeutralize with saturated aqueous NaHCO3, extract with ethyl acetate
  2. dry with materialdry over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-2cbcb79989624c00a760d518e634bdf6
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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