Potassium Hydroxide → HCID 15754280, compound

HRID 1461659Notes

Reaction equation

HRID 1461659 reaction equation
O=[C:2]([CH3:26])[CH2:3][N:4]([C:14]([CH3:25])([CH3:24])[C:15]1[CH:20]=[C:19]([Cl:21])[C:18]([Cl:22])=[C:17]([Cl:23])[CH:16]=1)[C:5](=[O:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[K+]>C(O)C>[CH3:26][C:2]1[CH2:3][N:4]([C:14]([CH3:25])([CH3:24])[C:15]2[CH:20]=[C:19]([Cl:21])[C:18]([Cl:22])=[C:17]([Cl:23])[CH:16]=2)[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19978930HCID 19978930, compound

Product 1

HCID 15754280HCID 15754280, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

40 g (96.9 mmol) of N-(2oxopropyl)-N-(3,4,5-trichloro-α,α-dimethylbenzyl)phenylacetamide (having a melting point of from 149° to 153° C.) prepared in accordance with the method of Reference Example 8, was dissolved in 500 ml of ethanol under heating, and 3.2 g (48.5 mmol) of potassium hydroxide powder was added thereto. The mixture was refluxed under heating for 10 minutes. The reaction solution was cooled, and then precipitated crystals were collected by filtration, washed with water and then air-dried. The filtrate was distilled under reduced pressure to remove the solvent, and then water was added thereto and extracted with ethyl acetate. The extract was washed with water and then dried over anhydrous magensium sulfate. The solvent was distilled off under reduced pressure to obtain crude crystals. This crude crystals and the crystals previously collected by filtration were put together and recrystallized from ethyl acetate to obtain 33.7 g (yield: 88.1%) of the desired compound as colorless crystals.

Workup

  1. customof from 149° to 153° C.
  2. customprepared in accordance with the method of Reference Example 8
  3. temperatureunder heating
  4. temperatureThe mixture was refluxed
  5. temperatureunder heating for 10 minutes
  6. temperatureThe reaction solution was cooled
  7. customprecipitated crystals
  8. filtrationwere collected by filtration
  9. washwashed with water
  10. customair-dried
  11. distillationThe filtrate was distilled under reduced pressure
  12. customto remove the solvent
  13. additionwater was added
  14. extractionextracted with ethyl acetate
  15. washThe extract was washed with water
  16. dry with materialdried over anhydrous magensium sulfate
  17. distillationThe solvent was distilled off under reduced pressure
  18. customto obtain crude crystals
  19. filtrationThis crude crystals and the crystals previously collected by filtration
  20. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4ae59752d80d40328a213938fceaa92c
Source dataset
uspto-grants-1991_12
Patent number
US05076834

Reaction notes

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