Chloroacetyl chloride → 5-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one

HRID 1857553Notes

Reaction equation

HRID 1857553 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]1=[O:14].[Cl:15][CH2:16][C:17](Cl)=[O:18]>C(=S)=S>[Cl:15][CH2:16][C:17]([C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[NH:5][C:6](=[O:14])[CH2:7]2)=[O:18]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 321710OxindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Aluminum chloride (30.8 g) and 2-oxindole (5.0 g) were added to 200 ml of carbon disulfide at room temperature and the mixture stirred. Chloroacetyl chloride (3.8 mL) was added and the stirring continued for 1 hour. The mixture was heated to reflux for 3 hours, cooled and the solvent decanted. The residue was stirred in ice water until it became a solid suspension. The solid was collected by vacuum filtration, washed in water, and dried to give 7.0 g (90% yield) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperaturecooled
  4. customthe solvent decanted
  5. stirringThe residue was stirred in ice water until it
  6. filtrationThe solid was collected by vacuum filtration
  7. washwashed in water
  8. customdried

Sources & evidence

ORD record
ord-4ddf0bc71e6c4577a0a9bc5a09ed789a
Source dataset
uspto-grants-2000_11
Patent number
US06147106

Reaction notes

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