p-Toluenesulfonic acid → 1-(3-Chlorophenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 413886Notes

Reaction equation

HRID 413886 reaction equation
[Cl: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>[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]([Cl: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

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 79323-ChloroanilineHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 102688021-(3-Chlorophenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

m-Chloroaniline (5 mmol, 0.6 g), 2-benzoyl-4-oxo-pentanoic acid ethyl ester (5 mmol, 1.2 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. Upon completion of the reaction, the crude solid was recrystallized from ethanol to provide the named product (m.p. 93.2° C.-94.6° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customUpon completion of the reaction
  4. customthe crude solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-98c9fe8dd6d04dc7a70045c79dfddcc6
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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