Water → HCID 19097813, compound

HRID 486297Notes

Reaction equation

HRID 486297 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:19][C:20](=O)[CH2:21][CH3:22])[C:9](=[O:18])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:4][C:3]=1[C:24]([F:27])([F:26])[F:25].[OH-].[Na+].O>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:19][C:20]([CH2:21][CH3:22])=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=3)[C:9]2=[O:18])=[CH:4][C:3]=1[C:24]([F:27])([F:26])[F:25]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 19097811HCID 19097811, compound

Product 1

HCID 19097813HCID 19097813, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.38 g (5.92 mmol) of N-(4-chloro-3-trifluoromethyl-phenyl)-N-(2-oxobutyl)-3-fluorophenylacetamide prepared in the same manner as in Example 3 were dissolved in 10 ml of ethanol, and 0.25 ml of a 10% aqueous sodium hydroxide solution was added at room temperature with stirring. The solution was stirred at the same temperature for 1 hour, and the reaction mixture was then poured into water, followed by extraction with ethyl acetate. Afterward, the resultant organic layer was dried over magnesium sulfate, and the solvent was then distilled off under reduced pressure. The precipitated crystals were collected by filtration, and then washed with n-hexane to obtain 1.93 g of the desired product in the state of colorless crystals (yield 85.0%).

Workup

  1. stirringThe solution was stirred at the same temperature for 1 hour
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialAfterward, the resultant organic layer was dried over magnesium sulfate
  4. distillationthe solvent was then distilled off under reduced pressure
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with n-hexane

Sources & evidence

ORD record
ord-e4ee034a6cb64399940ed8d9bee7c5f4
Source dataset
uspto-grants-1994_03
Patent number
US05290949

Reaction notes

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