Ammonia → (-)-2-(Pentafluorophenyl)propaneamide

HRID 2249003Notes

Reaction equation

HRID 2249003 reaction equation
[NH3:1].[F:2][C:3]1[C:8]([CH:9]([CH3:13])[C:10](Cl)=[O:11])=[C:7]([F:14])[C:6]([F:15])=[C:5]([F:16])[C:4]=1[F:17]>O>[F:2][C:3]1[C:8]([CH:9]([CH3:13])[C:10]([NH2:1])=[O:11])=[C:7]([F:14])[C:6]([F:15])=[C:5]([F:16])[C:4]=1[F:17]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 14651855(-)-2-(Pentafluorophenyl)propionyl chloride

Product 1

HCID 14651859(-)-2-(Pentafluorophenyl)propaneamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice-cooled 10 ml of concentrated aqueous ammonia, was added dropwise 2.5 g of (-)-2-(pentafluorophenyl)-propanoyl chloride obtained in Example 5. After stirring for 30 minutes at room temperature, the reaction mixture was diluted with water, extracted with ethyl acetate and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the subsequent recrystallization from a hexane-ether mixed solvent gave 1.92 g of (-)-2-(pentafluorophenyl)propaneamide as colorless needles having the aforementioned physical properties.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe subsequent recrystallization from a hexane-ether mixed solvent

Sources & evidence

ORD record
ord-4d56d54bc09047d3877240bbcb675e2f
Source dataset
uspto-grants-1991_08
Patent number
US05041641

Reaction notes

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