Carbon Tetrachloride → HCID 21262189, compound

HRID 567661Notes

Reaction equation

HRID 567661 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=2[CH3:16])[C:4](=[O:17])[N:3]1[CH3:18].[Cl:19]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>[Cl:19][C:5]1([C:8]2[C:9]([CH3:16])=[CH:10][C:11]([CH3:15])=[CH:12][C:13]=2[CH3:14])[C:6](=[O:7])[N:2]([CH3:1])[N:3]([CH3:18])[C:4]1=[O:17]

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 31398ChlorosuccinimideHCID 21262191HCID 21262191, compound

Product 1

HCID 21262189HCID 21262189, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 962WaterSolvent

Procedure

There was refluxed with heating a mixture of 0.50 g (2.0 mmols) of 1,2-dimethyl-4-(2,4,6-trimethylphenyl)pyrazolidine-3, 5-dione, 0.32 g (2.4 mmols) of N-chlorosuccinic acid imide, 19 mg (0.08 mmol) of benzoyl peroxide and 20 ml of carbon tetrachloride for 30 minutes. Water was added to the reaction mixture, followed by extraction with chloroform. The extract was washed with an aqueous solution of saturated sodium hydrogencarbonate and a saturated solution of sodium chloride and was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then the residue was washed with hexane, thereby obtaining 0.44 g (yield 78%) of 4-chloro-1,2-dimethyl-4-(2,4,6-trimethylphenyl)pyrazolidine-3,5-dione in the form of yellowish white crystals.

Workup

  1. temperatureThere was refluxed
  2. temperaturewith heating
  3. extractionfollowed by extraction with chloroform
  4. washThe extract was washed with an aqueous solution of saturated sodium hydrogencarbonate
  5. dry with materiala saturated solution of sodium chloride and was dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. washThen the residue was washed with hexane

Sources & evidence

ORD record
ord-4688d134786a45eeae4ba8b270127659
Source dataset
uspto-grants-2001_01
Patent number
US06180568B2

Reaction notes

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