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

HRID 365367Notes

Reaction equation

HRID 365367 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][C:7](Cl)=[O:8].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][C:11]1=[O:19]>C(=S)=S>[Cl:5][CH2:6][C:7]([C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[NH:10][C:11](=[O:19])[CH2:12]2)=[O:8]

Participants

5

Reactant 3

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

Product 1

HCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-oneYield 98.9%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a 250 ml round-bottomed flask equipped with condenser and nitrogen inlet were added 30.7 grams (230 mmol) aluminum chloride, 150 ml carbon disulfide, and 3.8 ml (48 mmol) chloroacetyl chloride. To the stirring mixture was added 5.0 grams (37 mmol) of oxindole portionwise over 15 minutes. The reaction was stirred a further 10 minutes, then refluxed 2 hours. The reaction was cooled, added to ice, stirred thoroughly, and the beige precipitate filtered, washed with water, and dried to afford 7.67 grams (97%) of 5-chloroacetyl-oxindole. NMR (d, DMSO-d6): 3.40 (s, 2H), 5.05 (s, 2H), 6.8-7.9 (m, 3H).

Workup

  1. customTo a 250 ml round-bottomed flask equipped with condenser and nitrogen inlet
  2. temperaturerefluxed 2 hours
  3. temperatureThe reaction was cooled
  4. additionadded to ice
  5. stirringstirred thoroughly
  6. filtrationthe beige precipitate filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-077f193df9814c5b8f2391f696c97e56
Source dataset
uspto-grants-2000_10
Patent number
US06127373

Reaction notes

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