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

HRID 842176Notes

Reaction equation

HRID 842176 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]([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>[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]([Cl:1])[CH:3]=2)[C:14]=1[CH3:15])=[O:26])[CH3:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 79323-ChloroanilineHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Product 1

HCID 98810561-(3-Chlorophenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

m-Chloroaniline (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 (0.1 g) were combined in ethanol, then heated under reflux. Upon completion of the reaction, the crude solid was recrystallized from ethanol to afford the desired product (m.p. 99.6° C.-100.5° 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-e051967b1fdc4d7c84ccf1c1304adf53
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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