p-Toluenesulfonic acid → HCID 10200016, compound

HRID 413890Notes

Reaction equation

HRID 413890 reaction equation
[Br: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]([C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:14][C:15](=O)[CH3:16])[CH3:10].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C.C(Cl)Cl>[CH2:9]([O:11][C:12]([C:13]1[CH:14]=[C:15]([CH3:16])[N:5]([C:4]2[CH:6]=[CH:7][CH:8]=[C:2]([Br:1])[CH:3]=2)[C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:26])[CH3:10]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 115623-BromoanilineHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 10200016HCID 10200016, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

m-Bromoaniline (5 mmol, 0.9 g), 2-benzoyl-4-oxo-pentanoic acid ethyl ester (5 mmol, 1.2 g), and tosic acid were combined in ethanol, then heated under reflux. The resulting oil was resuspended in methylene chloride, then washed with water, 5% sodium bicarbonate and brine. The organic layer was dried over MgSO4, then the solids were separated and the solvents evaporated under vacuum. The crude product was recrystallized from ethanol to yield the named product (m.p. 117.5° C.-119.2° 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 MgSO4
  5. customthe solids were separated
  6. customthe solvents evaporated under vacuum
  7. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-c233ae3cac754c20ac81d89d8ea4476f
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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