Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86709377, compound

HRID 2172200Notes

Reaction equation

HRID 2172200 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O1CCCCC1[O:24][C:25]1[CH:26]=[CH:27][C:28]([N:31]2[CH2:36][CH2:35][CH:34]([CH2:37][O:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][C:46]([F:49])([F:48])[F:47])=[CH:41][CH:40]=3)[CH2:33][CH2:32]2)=[N:29][CH:30]=1.C(=O)([O-])O.[Na+]>C(O)C>[F:49][C:46]([F:47])([F:48])[O:45][C:42]1[CH:43]=[CH:44][C:39]([O:38][CH2:37][CH:34]2[CH2:33][CH2:32][N:31]([C:28]3[CH:27]=[CH:26][C:25]([OH:24])=[CH:30][N:29]=3)[CH2:36][CH2:35]2)=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 86709378HCID 86709378, compound

Product 1

HCID 86709377HCID 86709377, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pyridinium p-toluenesulfonate (PPTS) (0.917 g) was added to an ethanol solution (20 ml) of 5′-(tetrahydropyran-2-yloxy)-4-(4-trifluoromethoxyphenoxymethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl (1.65 g), and the mixture was stirred for 4 hours while heating under reflux. After cooling the reaction mixture to room temperature, a sodium hydrogen carbonate aqueous solution was added thereto, and ethanol was distilled off under reduced pressure, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The solvent was distilled off and the precipitated solid was collected by filtration. The solid was then washed with diisopropyl ether and dried to afford the title compound as a yellow powder (0.94 g).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. distillationethanol was distilled off under reduced pressure
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off
  8. filtrationthe precipitated solid was collected by filtration
  9. washThe solid was then washed with diisopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-33d21823a64640bdbdddc0376906c812
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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