3-Aminobenzamide → 1-(3-Carbamoylphenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 413895

Reaction equation

HRID 413895 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[CH2:11]([O:13][C:14](=[O:28])[CH:15]([CH2:19][C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:16](=O)[CH3:17])[CH3:12].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:19]=[C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:1]([C:2]2[CH:10]=[CH:9][CH:8]=[C:4]([C:5](=[O:6])[NH2:7])[CH:3]=2)[C:16]=1[CH3:17])=[O:28])[CH3:12]

Participants

5

Reactant 3

HCID 16453-AminobenzamideHCID 6101p-Toluenesulfonic acidHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Product 1

HCID 99462861-(3-Carbamoylphenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Aminobenzamide (5 mmol, 1.0 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 precipitate was filtered from the mixture, then washed with ethanol. The white solid product was used without further purification (m.p. 237.8° C.-238.8° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. filtrationThe resulting precipitate was filtered from the mixture
  4. washwashed with ethanol
  5. customThe white solid product was used without further purification (m.p. 237.8° C.-238.8° C.)

Sources & evidence

ORD record
ord-1d32df0d2eae4b4b8b85a740ee769bc0
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Linked notes

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