Ethanol → HCID 22318053, compound

HRID 497060Notes

Reaction equation

HRID 497060 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]([CH2:16][C:17]([O:19]CC)=O)[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:26]([OH:28])[CH3:27]>>[C:26]([C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:17]([CH2:16][N:8]([C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)[C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:23][CH:22]=2)=[O:19])=[CH:10][CH:11]=1)(=[O:28])[CH3:27]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86591173HCID 86591173, compound

Product 1

HCID 22318053HCID 22318053, compound

Procedure

An ethanol solution of ethyl [(4-fluorobenzoyl)-(4-fluorophenyl)amino]acetate was mixed with 3 M sodium hydroxide aqueous solution and heated under reflux. The reaction solution was concentrated, the residue was mixed with 1 M hydrochloric acid and chloroform, the organic layer was separated, washed and dried and then the solvent was evaporated under a reduced pressure. A dichloromethane solution of the thus obtained carboxylic acid crude product was mixed with 4-aminoacetophenone and WSC.HCl in that order and then stirred. The reaction solution was mixed with 1 M hydrochloric acid, the organic layer was separated, washed and dried and then the solvent was evaporated under a reduced pressure. By purifying the thus obtained crude product by SCG, N-[(4-acetyl-phenylcarbamoyl)methyl]-4-fluoro-N-(4-fluorophenyl)benzamide (white foam) was obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. concentrationThe reaction solution was concentrated
  4. additionthe residue was mixed with 1 M hydrochloric acid and chloroform
  5. customthe organic layer was separated
  6. washwashed
  7. customdried
  8. customthe solvent was evaporated under a reduced pressure
  9. additionA dichloromethane solution of the thus obtained carboxylic acid crude product was mixed with 4-aminoacetophenone and WSC.HCl in that order
  10. additionThe reaction solution was mixed with 1 M hydrochloric acid
  11. customthe organic layer was separated
  12. washwashed
  13. customdried
  14. customthe solvent was evaporated under a reduced pressure
  15. customBy purifying the
  16. customthus obtained crude product by SCG

Sources & evidence

ORD record
ord-98186a4dd0f74dd8b22305c344f85f1c
Source dataset
uspto-grants-2005_09
Patent number
US06949543B2

Reaction notes

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