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

HRID 842182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 842182
Cl.[CH3:2][S:3]([C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH2:9])(=[O:5])=[O:4].[CH2:13]([O:15][C:16](=[O:30])[CH:17]([C:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:18][C:19](=O)[CH3:20])[CH3:14].C(N(CC)CC)C.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C.C(Cl)(Cl)Cl>[CH2:13]([O:15][C:16]([C:17]1[CH:18]=[C:19]([CH3:20])[N:9]([C:8]2[CH:10]=[CH:11][CH:12]=[C:6]([S:3]([CH3:2])(=[O:4])=[O:5])[CH:7]=2)[C:22]=1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:30])[CH3:14]

Komponenten

7

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 27351793-(Methylsulfonyl)aniline hydrochlorideHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Produkt 1

HCID 102933431-(3-Methanesulfonylphenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

3-Methylsulfonylaniline hydrochloride (5.8 mmol, 1.2 g), 2-benzoyl-4-oxo-pentanoic acid ethyl ester (5.8 mmol, 144 g), triethylamine (5.8 mmol, 0.61 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The resulting oil was resuspended in chloroform, then washed with water, 5% sodium bicarbonate, and brine. The organic layer was dried over NaSO44, then the solids were separated and solvents removed under vacuum. The crude material was purified over silica to yield the named product (m.p. 131° C.-133° C.).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux
  3. washwashed with water, 5% sodium bicarbonate, and brine
  4. customThe organic layer was dried over NaSO44
  5. customthe solids were separated
  6. customsolvents removed under vacuum
  7. customThe crude material was purified over silica

Quellen und Nachweise

ORD-Eintrag
ord-0f86e40f09554b94a257b38169915d9b
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372777B1

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