p-Toluenesulfonic acid monohydrate → HCID 68584607, compound

HRID 17323Notes

Reaction equation

HRID 17323 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]([C:15]1[C:16]([NH:30][C:31](=O)[C:32]([CH3:35])([CH3:34])[CH3:33])=[C:17]([OH:29])[C:18]([F:28])=[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:20]=1[CH3:21])#[N:14].O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:32]([C:31]1[O:29][C:17]2[C:16](=[C:15]([C:13]#[N:14])[C:20]([CH3:21])=[C:19]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:18]=2[F:28])[N:30]=1)([CH3:34])([CH3:33])[CH3:35]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86585896Sodium bicarbonate waterHCID 86630834N-(5-Cyano-2-fluoro-3-hydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

Product 1

HCID 68584607HCID 68584607, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (67 ml), p-toluenesulfonic acid monohydrate (98 mg, 515 μmol) were added to N-(5-cyano-2-fluoro-3-hydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide (I-73) (1.68 g, 5.15 mmol), followed by refluxing with a Dean-Stark condenser for 4 hours. After cooling, saturated sodium bicarbonate water (50 ml) was added to the reaction liquid, the product was extracted with ethyl acetate (200 ml). The organic layer was washed with saturated brine (50 ml×2), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1) to obtain the entitled compound (1.44 g, 91%) as a colorless solid.

Workup

  1. temperatureby refluxing with a Dean-Stark condenser for 4 hours
  2. temperatureAfter cooling
  3. extractionthe product was extracted with ethyl acetate (200 ml)
  4. washThe organic layer was washed with saturated brine (50 ml×2)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-3e287d6445b4440997f3b90580712086
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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