HCID 10493689, compound → HCID 10637355, compound

HRID 2395197Notes

Reaction equation

HRID 2395197 reaction equation
[F:1][C:2]([F:20])([CH:17]([F:19])[F:18])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][NH:13][C:12]2=[O:16])=[CH:7][CH:6]=1.[H][H]>[C].[Pd].C(O)(=O)C>[F:20][C:2]([F:1])([CH:17]([F:19])[F:18])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 10493689HCID 10493689, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10637355HCID 10637355, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 10 ml of acetic acid and 2.0 g of 1-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2-(1H,3H)-imidazolone was added 0.5 g of 10% palladium-carbon. The mixture was stirred in a hydrogen atmosphere for 7.5 hours. The catalyst was separated by filtration, washed with acetic acid and the filtrate and the washing were collected, followed by distilling off the solvent under reduced pressure. To the residue were added 40 ml of water and 40 ml of ethyl acetate to fractionate, and the ethyl acetate phase was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. to give colorless crystals. The obtained colorless crystals were washed with diisopropyl ether to give 1.86 g of 1-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2-imidazolidinone as colorless crystals.

Workup

  1. customThe catalyst was separated by filtration
  2. washwashed with acetic acid
  3. customthe filtrate and the washing were collected
  4. distillationby distilling off the solvent under reduced pressure
  5. additionTo the residue were added 40 ml of water and 40 ml of ethyl acetate
  6. dry with materialthe ethyl acetate phase was dried over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto give colorless crystals
  9. washThe obtained colorless crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-3e3d0076763e40dfad31acc13dfbb7d5
Source dataset
uspto-grants-1998_09
Patent number
US05814324

Reaction notes

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