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

HRID 1390169Notes

Reaction equation

HRID 1390169 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-fb7f58545c634bafb71c8d42c5bd33ff
Source dataset
uspto-grants-1979_02
Patent number
US04138243

Reaction notes

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