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

HRID 413889

Reaction equation

HRID 413889 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]([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.C(Cl)Cl>[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:1]([C:2]2[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=2)[C:14]=1[CH3:15])=[O:26])[CH3:10]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7934m-ToluidineHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Product 1

HCID 99015912-Methyl-5-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), 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. The resulting oil was resuspended in methylene chloride, then washed with water, 5% sodium bicarbonate, and brine. The organic layer was dried over NaSO4, 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. 103° C.-104.5° 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
  5. customthe solids were separated
  6. customthe solvents evaporated under vacuum
  7. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-ff68f960f8ac4d6d90905ce201ac2237
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Linked notes

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