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

HRID 413896Notes

Reaction equation

HRID 413896 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]([C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:16][C:17](=O)[CH3:18])[CH3:12].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:16]=[C:17]([CH3:18])[N:1]([C:2]2[CH:10]=[CH:9][CH:8]=[C:4]([C:5](=[O:6])[NH2:7])[CH:3]=2)[C:20]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:28])[CH3:12]

Participants

5

Reactant 3

HCID 16453-AminobenzamideHCID 6101p-Toluenesulfonic acidHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 101547701-(3-Carbamoylphenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Aminobenzamide (5 mmol, 1.0 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 precipitate was filtered from the reaction mixture, then washed with ethanol. The tan solid product was used without further purification (m.p. 208.9° C.-210.3° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. filtrationThe resulting precipitate was filtered from the reaction mixture
  4. washwashed with ethanol
  5. customThe tan solid product was used without further purification (m.p. 208.9° C.-210.3° C.)

Sources & evidence

ORD record
ord-eaf992b871da46a58b71d23dbf0e4ab0
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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