Chloride → HCID 21248387, compound

HRID 620017Notes

Reaction equation

HRID 620017 reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][C:7]1([CH3:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:16].[Cl-]>C(=S)=S>[CH3:6][C:7]1([CH3:17])[C:15]2[C:10](=[CH:11][C:12]([C:3](=[O:4])[CH2:2][Br:1])=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:16]

Participants

5

Reactant 3

HCID 312ChlorideHCID 89602Bromoacetyl chlorideHCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-one

Product 1

HCID 21248387HCID 21248387, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

bromoacetyl chloride (9.76 g) is added dropwise to a stirred mixture of 3,3-dimethyloxindole (5 g) and aluninum chloride (10.33 g) in carbon disulfide (100 ml). The reaction mixture is stirred at reflux overnight and cooled. The solvent is decanted, and a mixture of ice and water poured into the residue. Methylene chloride is added to the mixture, which is filtered. The filtrate is separated, the aqueous layer is extracted with methylene chloride and the combined organic extracts are washed with sat'd aqueous sodium bicarbonate, dried, filtered, concentrated, and recrystallized from boiling isopropanol, affording the desired product, M.P.=230°-232° C.

Workup

  1. temperatureat reflux overnight
  2. temperaturecooled
  3. customThe solvent is decanted
  4. additiona mixture of ice and water
  5. additionpoured into the residue
  6. additionMethylene chloride is added to the mixture, which
  7. filtrationis filtered
  8. customThe filtrate is separated
  9. extractionthe aqueous layer is extracted with methylene chloride
  10. washthe combined organic extracts are washed with sat'd aqueous sodium bicarbonate
  11. customdried
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customrecrystallized

Sources & evidence

ORD record
ord-a8db1df4624644bfbcf99500e61fac2f
Source dataset
uspto-grants-1989_04
Patent number
US04818755

Reaction notes

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