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

HRID 842174Notes

Reaction equation

HRID 842174 reaction equation
Cl.Cl.[CH3:3][N:4]([CH3:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1.C(N(CC)CC)C.[CH2:20]([O:22][C:23](=[O:37])[CH:24]([CH2:28][C:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:25](=O)[CH3:26])[CH3:21].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:20]([O:22][C:23]([C:24]1[CH:28]=[C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([N:4]([CH3:12])[CH3:3])[CH:6]=2)[C:25]=1[CH3:26])=[O:37])[CH3:21]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 771241,3-Benzenediamine, N1,N1-dimethyl-, hydrochloride (1:2)HCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Product 1

HCID 101324961-(3-Dimethylaminophenyl)-2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N,N-dimethyl-1,3-phenylenediamine dihydrochloride (5 mmol, 1.09), triethylamine (10 mmol, 1.4 mL), 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 (25 mL), then heated under reflux (12 hrs). The solvents were removed under vacuum, the resulting oil was redissolved in methylene chloride, then applied to a silica column. The purified product was collected as a translucent oil. The named compound was identified by 1H-NMR (CDCl3, ppm) 1.28 t (3H) , 2.35 s (3H) , 2.77 s (6H) , 4.2 q (2H) , 6.3-6.7 m (4H), and 7.0-7.3 m (5H).

Workup

  1. temperatureheated
  2. temperatureunder reflux (12 hrs)
  3. customThe solvents were removed under vacuum
  4. dissolutionthe resulting oil was redissolved in methylene chloride
  5. customThe purified product was collected as a translucent oil

Sources & evidence

ORD record
ord-57cba9d4b99e4d1084d75663f68338a3
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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