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

HRID 1762091Notes

Reaction equation

HRID 1762091 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 N2 inlet were added 30.7 g (230 mmol) aluminum chloride, 150 ml carbon disulfide, and 3.8 ml (48 mmol) chloroacetyl chloride. To the stirring mixture was added 5.0 g (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 g (97%) of 5-chloroacetyloxindole. 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 N2 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-5d4cc84dc83b4681ba41c562656919f1
Source dataset
uspto-grants-1989_05
Patent number
US04831031

Reaction notes

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