p-Toluenesulfonic acid → 5-Methyl-2-phenyl-1-m-tolyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 842177Notes

Reaction equation

HRID 842177 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1.[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:1]([C:2]2[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=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 7934m-ToluidineHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 99230435-Methyl-2-phenyl-1-m-tolyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

m-Toluidine (5 mmol, 0.5 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. The resulting oil was resuspended in methylene chloride, then washed with water, 5% sodium bicarbonate, and brine. The organic layer was dried over NaSO4 (sodium sulfate), the solids were separated, and the solvents evaporated under vacuum. The crude product was recrystallized from ethanol to yield the named product (m.p. 92.5° C.-94.0° 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 (sodium sulfate)
  5. customthe solids were separated
  6. customthe solvents evaporated under vacuum
  7. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-08cdbd3fc0d04504ba7e0b113c813952
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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