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

HRID 413885

Reaktionsgleichung

Reaktionsgleichung von HRID 413885
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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N,N-dimethyl-1,3-phenylenediamine dihydrochloride (5 mmol, 1.0 g), 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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1018c1edffcf433f8cded781d00d00c1
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06569890B2

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