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Potassium Iodide → 6-Chloro-3,3-bis[(3-chlorophenyl)methyl]-1,3-dihydro-2H-indol-2-one

HRID 2102656
Notes
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Reaction equation

HRID 2102656 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=O)[NH:8]2)=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Br.[I-].[K+].[C:23](=[O:26])([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:7][C:4]3[CH:5]=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=3)([CH2:16][C:15]3[CH:18]=[CH:19][CH:20]=[C:13]([Cl:12])[CH:14]=3)[C:23](=[O:26])[NH:8]2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 7363446-Chloro-1,3-dihydroindol-2-one

Product 1

HCID 578030756-Chloro-3,3-bis[(3-chlorophenyl)methyl]-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 180
Acetone
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-chlorooxindole (0.42 g, 2.5 mmol) (Crescent), 3-chlorobenzyl bromide (1.13 g, 5.5 mmol) (Aldrich), potassium iodide (1.04 g, 6.25 mmol) and potassium carbonate (1.04 g, 7.5 mmol) in acetone (10 mL) was heated at 60° C. for 20 hours in a sealed tube. After cooling, mixture was diluted with ethyl acetate (50 mL) and extracted with water (50 mL) and brine (50 mL). Aqueous layers were back washed with ethyl acetate (50 mL). Organic layers were combined, dried (MgSO4), filtered and concentrated. Residue was recrystallized from ethyl acetate-hexanes to give 6-chloro-3,3-bis-(3-chlorobenzyl)-1,3-dihydro-indol-2-one as white needles. (Yield 0.31 g, 29.8%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with water (50 mL) and brine (50 mL)
  3. washAqueous layers were back washed with ethyl acetate (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customResidue was recrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-5e049112aba740ff81c8ced8d1eb3cd7
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576082B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes