18-Crown-6 → N-(3',4'-Dichlorophenyl)-3,4-dimethyl-2-fluoro-5-oxo-2,5-dihydropyrrole

HRID 27188Notes

Reaction equation

HRID 27188 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]2O)[CH:5]=[CH:6][C:7]=1[Cl:8].[F-:18].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]2[F:18])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 13069714N-(3',4'-Dichlorophenyl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole

Product 1

HCID 13069717N-(3',4'-Dichlorophenyl)-3,4-dimethyl-2-fluoro-5-oxo-2,5-dihydropyrrole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

23.2 g N-(3,4-dichlorophenyl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole (see Example 3) is refluxed together with 11.6 g of potassium fluoride and 0.3 g of 18-crown-6 (cyclic polyethylene ether) in 50 ml of acetonitrile for 14 hours. After cooling, undissolved constituents are filtered off, and the filtrate is concentrated by evaporation. The residue is recrystallised from methanol to yield 8 g (35% of theory) of the above product in the form of colourless crystals, m.p. 102°-103°.

Workup

  1. temperatureAfter cooling
  2. filtrationundissolved constituents are filtered off
  3. concentrationthe filtrate is concentrated by evaporation
  4. customThe residue is recrystallised from methanol
  5. customto yield 8 g (35% of theory) of the above product in the form of colourless crystals, m.p. 102°-103°

Sources & evidence

ORD record
ord-af1197486d4747b380c66b1cb854ec1e
Source dataset
uspto-grants-1980_09
Patent number
US04220655

Reaction notes

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