Potassium Iodide → HCID 19874550, compound

HRID 465455Notes

Reaction equation

HRID 465455 reaction equation
[CH2:1]([C:5]1[CH:22]=[CH:21][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br)=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].Cl.[NH:30]1[CH2:34][CH2:33][C:32](=[O:35])[NH:31]1.[I-].[K+]>C(#N)C.O>[CH2:1]([C:5]1[CH:22]=[CH:21][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:30]2[CH2:34][CH2:33][C:32](=[O:35])[NH:31]2)=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27337123-Pyrazolidinone hydrochlorideHCID 19874510HCID 19874510, compound

Product 1

HCID 19874550HCID 19874550, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of 10-(4-acetonylphenoxy)decylbromide, ethylene ketal (3.0 g), potassium carbonate (3.8 g), pyrazolidin-3-one hydrochloride (1.47 g) and potassium iodide (0.5 g) in acetonitrile:water (95:5), was heated under reflux for 3 hr. The reaction mixture was allowed to cool, filtered and the solvent evaporated in vacuo. The residue was dissolved in chloroform, washed with water (2×50 ml), dried (magnesium sulphate), fitered and the solvent removed in vacuo. The residue was dissolved in acetone (50 ml) and treated with 2M hydrochloric acid solution (3 ml) and allowed to stand at room temperature for 3 hr. The solvent was removed in vacuo and the residue was dissolved in chloroform and washed with 1.2M sodium bicarbonate solution (1×50 ml), water (2×50 ml), dried (magnesium sulphate), filtered and the solvent removed in vacuo to give 1-[10-(4-acetonylphenoxy)decyl]pyrazolidin-3-one (0.66 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hr
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. dissolutionThe residue was dissolved in chloroform
  7. washwashed with water (2×50 ml)
  8. dry with materialdried (magnesium sulphate)
  9. customthe solvent removed in vacuo
  10. dissolutionThe residue was dissolved in acetone (50 ml)
  11. additiontreated with 2M hydrochloric acid solution (3 ml)
  12. customThe solvent was removed in vacuo
  13. dissolutionthe residue was dissolved in chloroform
  14. washwashed with 1.2M sodium bicarbonate solution (1×50 ml), water (2×50 ml)
  15. dry with materialdried (magnesium sulphate)
  16. filtrationfiltered
  17. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-bcf9f90175924dc1bdf3931b33b96a7d
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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