18-Crown-6 → HCID 178524593, compound

HRID 466158Notes

Reaction equation

HRID 466158 reaction equation
[F-].[K+].C1OCCOCCOCCOCCOCCOC1.[Br:21][C:22]1[C:23]([O:37]C(=O)C2C=CC=CC=2)=[CH:24][C:25]([O:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:26][CH:27]=1>C(#N)C>[C:29]([O:28][C:25]1[CH:24]=[C:23]([OH:37])[C:22]([Br:21])=[CH:27][N:26]=1)(=[O:36])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 14049627HCID 14049627, compound

Product 1

HCID 178524593HCID 178524593, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

There were mixed 0.15 g of potassium fluoride, 0.35 g of 18-crown-6 and 50 ml of acetonitrile. The mixture was refluxed for 30 minutes and 0.50 g of 5-bromo-2,4-dibenzoyloxypyridine was added thereto. The mixture was refluxed overnight, left to stand for cooling and concentrated. The concentrate was extracted with ethyl acetate and washed with water. The ethyl acetate layer was concentrated and the concentrate was treated with ether, giving 0.23 g of the title compound in a yield of 62%.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. temperatureThe mixture was refluxed overnight
  3. waitleft
  4. temperaturefor cooling
  5. concentrationconcentrated
  6. extractionThe concentrate was extracted with ethyl acetate
  7. washwashed with water
  8. concentrationThe ethyl acetate layer was concentrated
  9. additionthe concentrate was treated with ether

Sources & evidence

ORD record
ord-72fdcc551a0547df9769e1a0c03b399a
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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