Sodium Hydroxide → HCID 15754299, compound

HRID 1461658Notes

Reaction equation

HRID 1461658 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[C:5]([N:8]([CH2:19][C:20](=O)[CH3:21])[C:9](=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])([CH3:7])[CH3:6].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[C:5]([N:8]1[CH2:19][C:20]([CH3:21])=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[C:9]1=[O:18])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19978931HCID 19978931, compound

Product 1

HCID 15754299HCID 15754299, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.8 g (17 mmol) of N-(3,5-dichloro-α,α-dimethylbenzyl)-N-(2-oxopropyl)-2-fluorophenylacetamide (having a melting point of from 167° to 170° C.) prepared in accordance with the method of Reference Example 8, was dissolved in 30 ml of ethanol, and 0.7 g (11 mmol) of sodium hydroxide powder was added thereto. The mixture was refluxed under heating for 10 minutes. The reaction solution was cooled, and then ethanol was distilled off under reduced pressure. Water was added to the residue and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The crude crystals thereby obtained was recrystallized from methanol to obtain 3.1 g (yield: 49%) of the desired compound as colorless crystals.

Workup

  1. customof from 167° to 170° C.
  2. customprepared in accordance with the method of Reference Example 8
  3. temperatureThe mixture was refluxed
  4. temperatureunder heating for 10 minutes
  5. temperatureThe reaction solution was cooled
  6. distillationethanol was distilled off under reduced pressure
  7. additionWater was added to the residue
  8. extractionextracted with ethyl acetate
  9. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe crude crystals thereby obtained
  12. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-e2d4af888f1b412796ad69ac6c0f033a
Source dataset
uspto-grants-1991_12
Patent number
US05076834

Reaction notes

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