Potassium Carbonate → HCID 86668441, compound

HRID 2040927Notes

Reaction equation

HRID 2040927 reaction equation
[F:1][CH:2]([F:5])[CH2:3]Cl.[C:6]1(=[O:12])[NH:10][C:9](=[O:11])[CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[F:1][CH:2]([F:5])[CH2:3][N:10]1[C:6](=[O:12])[CH2:7][CH2:8][C:9]1=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11439SuccinimideHCID 2736499Chlorodifluoroethane (mixed isomers)

Product 1

HCID 86668441HCID 86668441, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

An amount of 40.9 g (0.39 mol) of 2,2-difluoro-1-chloroethane, 3.22 g (9.9 mmol) of tetra(n-butyl)ammonium bromide, 95 g of N,N-dimethylformamide and 20 g (0.19 mol) of succinimide are treated with 83.6 g (0.599 mol) of potassium carbonate. The reaction mixture is stirred in an autoclave under pressure at 120° C. for 16 h. After the end of the reaction, cooling is carried out to ambient temperature and the reaction mixture is subsequently filtered. The filter residue is washed with dichloromethane and the solvent is removed under vacuum. The oil is once more treated with 30 ml of water and extracted twice with 30 ml of dichloromethane. The combined organic phases are dried and the solvent is removed under vacuum. An amount of 27.3 g of 1-(2,2-difluoroethyl)pyrrolidine-2,5-dione with a purity of 93% is obtained. This corresponds to a yield of 77.8% of theory.

Workup

  1. customAfter the end of the reaction
  2. temperaturecooling
  3. customis carried out to ambient temperature
  4. filtrationthe reaction mixture is subsequently filtered
  5. washThe filter residue is washed with dichloromethane
  6. customthe solvent is removed under vacuum
  7. additionThe oil is once more treated with 30 ml of water
  8. extractionextracted twice with 30 ml of dichloromethane
  9. customThe combined organic phases are dried
  10. customthe solvent is removed under vacuum

Sources & evidence

ORD record
ord-6b12818571bf429c8d7d8c3af895b4ec
Source dataset
uspto-grants-2013_11
Patent number
US08580973B2

Reaction notes

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