3-Chloropyrrolidine-2,5-dione → HCID 66692113, compound

HRID 1662137Notes

Reaction equation

HRID 1662137 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:12][C:13]#[CH:14])([CH3:4])([CH3:3])[CH3:2].[Cl:15]C1CC(=O)NC1=O>CC(C)=O.C([O-])(=O)C.[Ag+]>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:12][C:13]#[C:14][Cl:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 144005023-Chloropyrrolidine-2,5-dioneHCID 61343954HCID 61343954, compound

Product 1

HCID 66692113HCID 66692113, compound

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 180AcetoneSolvent

Procedure

To a solution of Example 5A (18.86 g, 100 mmol) in acetone (400 mL) was added N chlorosuccinimide (16.02 g, 120 mmol) and silver acetate (1.67 g, 10 mmol) and the mixture was heated at reflux for 4 hours. After cooling, the silver salts were removed by filtration and the filtrate evaporated under reduced pressure. The residue was taken up in diethyl ether, washed with water and saturated aqueous sodium bicarbonate, dried with magnesium sulfate, filtered, and the solvent was removed under reduced pressure to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.38 (s, 9H), 4.73 (s, 2H), 6.91-6.97 (m, 2H), 7.19 (td, J=7.71, 1.86 Hz, 1H), 7.30 (dd, J=7.97, 1.53 Hz, 1H). MS (DCI) m/z 223 (M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. temperatureAfter cooling
  4. customthe silver salts were removed by filtration
  5. customthe filtrate evaporated under reduced pressure
  6. washwashed with water and saturated aqueous sodium bicarbonate
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6c55d1c3c2b84d01b1951066490d7501
Source dataset
uspto-grants-2011_10
Patent number
US08030504B2

Reaction notes

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