p-Toluenesulfonic acid → HCID 10268111, compound

HRID 413902Notes

Reaction equation

HRID 413902 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH2:9]([O:11][C:12](=[O:26])[CH:13]([CH2:17][C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:14](=O)[CH3:15])[CH3:10].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C.C(Cl)(Cl)Cl>[CH2:9]([O:11][C:12]([C:13]1[CH:17]=[C:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:5]([C:4]2[CH:6]=[CH:7][CH:8]=[C:2]([F:1])[CH:3]=2)[C:14]=1[CH3:15])=[O:26])[CH3:10]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 97423-FluoroanilineHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Product 1

HCID 10268111HCID 10268111, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

m-Fluoroaniline (5 mmol, 0.6 g), 3-oxo-2-(2-oxo-2-phenyl-ethyl)-butyric acid ethyl ester (5 mmol, 1.2 g), and tosic acid were combined in ethanol, then heated under reflux. The resulting solid was resuspended in chloroform, then washed with water, 5% sodium bicarbonate, and brine. The organic layer was dried over NaSO4, then the solids were separated and the solvents removed under vacuum. The named product was recrystallized from ethanol (m.p. 96.3° C.-98.0° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. washwashed with water, 5% sodium bicarbonate, and brine
  4. dry with materialThe organic layer was dried over NaSO4
  5. customthe solids were separated
  6. customthe solvents removed under vacuum
  7. customThe named product was recrystallized from ethanol (m.p. 96.3° C.-98.0° C.)

Sources & evidence

ORD record
ord-f5419339ae0c4d8f90a7ac795591da2f
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

Loading…