Pyridine → HCID 20031857, compound

HRID 2291294Notes

Reaction equation

HRID 2291294 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[F:14][C:15]1[C:20]([OH:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:16]=1[F:25].N1C=CC=CC=1>C(#N)C>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:21][C:20]2[C:19]([F:22])=[C:18]([F:23])[C:17]([F:24])=[C:16]([F:25])[C:15]=2[F:14])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 13041PentafluorophenolHCID 2756254p-Acetoxybenzoyl chloride

Product 1

HCID 20031857HCID 20031857, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 10.8 g of 4-acetoxybenzoyl chloride in dry acetonitrile was treated with 10 g of pentafluorophenol, and stirred at 0° C. whilst 4.4 ml of pyridine was added dropwise. The solution was permitted to warm to room temperature then heated to reflux temperature until the reaction was complete. Solvent was evaporated in vacuo and the residue obtained partitioned between ethyl acetate and water. The organic solution was washed with further portions of water and brine and dried over magnesium sulphate. Evaporation afforded 18 g of the title compound.

Workup

  1. additionwas added dropwise
  2. temperaturethen heated
  3. temperatureto reflux temperature until the reaction
  4. customSolvent was evaporated in vacuo
  5. customthe residue obtained
  6. custompartitioned between ethyl acetate and water
  7. washThe organic solution was washed with further portions of water and brine
  8. dry with materialdried over magnesium sulphate
  9. customEvaporation

Sources & evidence

ORD record
ord-24df95033cc34585a96c580da67cb244
Source dataset
uspto-grants-1989_01
Patent number
US04795748

Reaction notes

Loading…