Methanesulfonic Acid → HCID 67594112, compound

HRID 442881Notes

Reaction equation

HRID 442881 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6](O)[C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]1[C:26]([O:28][CH2:29][CH3:30])=[O:27].CS(O)(=O)=O.[OH-].[Na+].[Cl-].[NH4+]>C(Cl)Cl>[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[C:19]2[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:17][C:18]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 73125Ethyl indole-2-carboxylateHCID 1230494,4'-Difluorobenzhydryl alcohol2×

Product 1

HCID 67594112HCID 67594112, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,4'-difluorobenzhydrol (12.8 g, 58.1 mmol) and ethyl indole-2-carboxylate (10.0 g, 52.9 mmol) in 100 ml of methylene chloride was added methanesulfonic acid (3.4 ml, 52.9 mmol), followed by stirring at room temperature for one hour. Then, 4,4'-difluorobenzhydrol (1.0 g, 4.54 mmol) was further added to the reaction mixture followed by stirring for 1.5 hours to complete the reaction. A 2N aqueous sodium hydroxide solution was added to the reaction solution, and a saturated aqueous solution of ammonium chloride was further added thereto for neutralization followed by extraction with chloroform. The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give a crude product. The obtained crude product was recrystallized from ethanol to give 8.4 g (yield: 40%) of the title compound.

Workup

  1. stirringby stirring for 1.5 hours
  2. customthe reaction
  3. extractionfor neutralization followed by extraction with chloroform
  4. washThe resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto give a crude product
  8. customThe obtained crude product
  9. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-4ea5a04975c848e18b714b660dc77820
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

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