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

HRID 1387399Notes

Reaction equation

HRID 1387399 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 79%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

The following reagents were combined in the order listed under nitrogen at room temperature: aluminum chloride (17 g, 0.130 moles), carbon disulfide (40 mL), chloroacetyl chloride (3.01 g, 0.027 moles), and oxindole (2.73 g, 0.021 moles). The reaction mixture was warmed to reflux and stirring continued at this temperature for 3 h. The reaction was cooled to room temperature and the liquid was carefully decanted off. Ice water was added dropwise to the remaining residue under nitrogen (slowly and carefully). Addition of water was ceased when a total of 50 mL had been added and the reaction was stirred for 1 h at room temperature. The tan solid was collected by filtration, washed 3 times with water and dried in vacuo at 72° C. to give a light tan solid (3.4 g, 79% yield). 1H NMR (DMSO-d6) δ3.62 (s, 2H); 5.15 (s, 2H); 6.96 (d, 1H); 7.84 (s, 1H); 7.91 (d, 2H); 10.84 (bs, 1H). APCI-MS m/z 208 (M−H).

Workup

  1. customlisted under nitrogen at room temperature
  2. temperatureThe reaction mixture was warmed
  3. temperatureto reflux
  4. customthe liquid was carefully decanted off
  5. additionIce water was added dropwise to the remaining residue under nitrogen (slowly and carefully)
  6. additionAddition of water
  7. additionhad been added
  8. stirringthe reaction was stirred for 1 h at room temperature
  9. filtrationThe tan solid was collected by filtration
  10. washwashed 3 times with water
  11. customdried in vacuo at 72° C.

Sources & evidence

ORD record
ord-8497515e37934c80a715673dfd1c6b92
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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