Chloroacetyl chloride → HCID 10125459, compound

HRID 2245542Notes

Reaction equation

HRID 2245542 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Br:6][C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][C:12](=[O:16])[NH:13]2)=[CH:9][CH:8]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[Br:6][C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][C:12](=[O:16])[NH:13]2)=[CH:9][C:8]=1[C:3](=[O:4])[CH2:2][Cl:1]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 27732896-bromo-2,3-dihydro-1H-indol-2-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10125459HCID 10125459, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

Chloroacetyl chloride (0.65 mL, 8.2 mmol) was added to a cooled (0° C.) suspension of 6-bromooxindol (0.825 g, 3.9 mmol) and aluminium chloride (1.82 g, 13.6 mmol) in 1,2-dichloroethane (8 mL). The resulting mixture was stirred at 0° C. for 20 min and at 50° C. for 17 h. The mixture was cooled to room temperature and was then poured on ice. The formed solid was filtered off, washed with water, and dried in vacuo to give 1.10 g (99% yield) of the title compound: 1H NMR (DMSO-d6, 400 MHz) δ 7.69 (s, 1H), 7.09 (s, 1H), 4.97 (s, 2H), 3.52 (s, 2H).

Workup

  1. temperaturea cooled
  2. temperatureThe mixture was cooled to room temperature
  3. additionwas then poured on ice
  4. filtrationThe formed solid was filtered off
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-bb25f6f104944159b2dc567fe2f18a4c
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

Loading…