Potassium Carbonate → HCID 15463509, compound

HRID 430788Notes

Reaction equation

HRID 430788 reaction equation
C([NH:4][CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH2:16][C:17]([O:19]C)=[O:18])[C:9]=2[O:8][CH:7]=1)(=O)C.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:29]([S:36](Cl)(=[O:38])=[O:37])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>Cl>[CH2:29]([S:36]([NH:4][CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH2:16][C:17]([OH:19])=[O:18])[C:9]=2[O:8][CH:7]=1)(=[O:38])=[O:37])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 74740Phenylmethanesulfonyl chlorideHCID 53784183HCID 53784183, compound

Product 1

HCID 15463509HCID 15463509, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Conditions

Temperature
80 °C

Procedure

To 1N hydrochloric acid (10 ml), methyl (3-acetylaminomethylbenzofuran-7-yloxy)acetate (145 mg) was added and the obtained mixture was heated to reflux for 5 hours. To the reaction mixture, 2N aqueous sodium hydroxide solution (5 ml) was added to neutralize the mixture, and potassium carbonate (1.46 g) and benzylsulfonyl chloride (1.48 g) were added to the mixture, followed by stirring the resultant at 80° C. for one day and night. To the resulting mixture, 1N hydrochloric acid was added to neutralize the mixture and the resultant was extracted with ethyl acetate (3×20 ml). The organic layers were washed with saturated brine and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure and the obtained solids were purified by recrystallization (ethyl acetate/n-hexane) to obtain the desired compound (85 mg, yield: 43%).

Workup

  1. temperaturethe obtained mixture was heated
  2. temperatureto reflux for 5 hours
  3. additionwere added to the mixture
  4. extractionthe resultant was extracted with ethyl acetate (3×20 ml)
  5. washThe organic layers were washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customAfter removing solids
  8. filtrationby filtration
  9. customthe solvent was removed under reduced pressure
  10. customthe obtained solids were purified by recrystallization (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-fa32f8a3bb15406abfd936859a5218de
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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