p-Toluenesulfonic acid → Ethyl1-(3-bromophenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylate

HRID 842179Notes

Reaction equation

HRID 842179 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 10200016Ethyl1-(3-bromophenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylate

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-29a12cdb837f411eae18ff3a5b3eb764
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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