Hydrochloric Acid → 3-(2-Benzofuran-1(3H)-ylidene)-5-chloro-1,3-dihydro-2H-indol-2-one

HRID 1263709Notes

Reaction equation

HRID 1263709 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[C:12]1([C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][O:14]1)=O.C[Si](C)(C)N[Si](C)(C)C.[Na].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][O:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6885Phthalide2×HCID 1528015-ChlorooxindoleHCID 45051731Sodium hexamethyidisilazane

Product 1

HCID 696590113-(2-Benzofuran-1(3H)-ylidene)-5-chloro-1,3-dihydro-2H-indol-2-oneYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution containing 5-chlorooxindole (0.30 g, 1.79 mmol) and phthalide (0.312 g, 2.33 mmol) in 6.0 mL of dimethylformamide (DMF) was added 3.76 mL of sodium hexamethyldisilazane (1.0 M in tetrahydrofuran (THF)) over 1 min. The solution was stirred at room temperature for 25 min and then 85 mg (0.634 mmol) phthalide was added. After an additional 20 min at room temperature the mixture was poured into 70 mL of 4% aqueous HCl solution to give a yellow solid. The aqueous mixture was extracted with EtOAc and the organic phase washed with saturated NaHCO3, brine and then dried with Na2SO4. After removal of the solvent in vacuo, the solid residue was recrystallized from MeOH/EtOAc to afford the title (141 mg, 28%) compound as a yellow solid.

Workup

  1. customto give a yellow solid
  2. extractionThe aqueous mixture was extracted with EtOAc
  3. washthe organic phase washed with saturated NaHCO3, brine
  4. dry with materialdried with Na2SO4
  5. customAfter removal of the solvent in vacuo
  6. customthe solid residue was recrystallized from MeOH/EtOAc

Sources & evidence

ORD record
ord-95b7c147a17742b5b6d12fdd61493a86
Source dataset
uspto-grants-2003_04
Patent number
US06541504B1

Reaction notes

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