Pyrrole → (2-Chloro-3-nitrophenyl)-1H-pyrrol-1-ylmethanone

HRID 895158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 895158
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[NH:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1)=[O:6]

Komponenten

8

Edukt 4

HCID 8027PyrroleHCID 8471TriethylamineHCID 198702-Chloro-3-nitrobenzoic acidHCID 24386Thionyl Chloride

Produkt 1

HCID 22385748(2-Chloro-3-nitrophenyl)-1H-pyrrol-1-ylmethanoneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Chloro-3-nitrobenzoic acid (2 g, 10.0 mmol) and thionyl chloride (30 ml) were mixed at room temperature, and 4-dimethylaminopyridine (122 mg, 1.00 mmol) was added. The reaction mixture was refluxed for 12 hours and then concentrated to give a crude acid chloride. The acid chloride mentioned above was added to a solution of pyrrole (3.5 ml, 50.0 mmol) and triethylamine (7.0 ml, 50.0 mmol) in methylene chloride (80 ml) at room temperature. The reaction mixture was stirred at the same temperature for 6 hours and diluted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, filtered, and concentrated to give a crude compound. The crude compound was purified by silica gel column chromatography (hexane:ethyl acetate, 1:0-7:3) to give the title compound (2.43 g) as a yellow oil.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. concentrationconcentrated
  3. customto give a crude acid chloride
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude compound
  9. customThe crude compound was purified by silica gel column chromatography (hexane:ethyl acetate, 1:0-7:3)

Quellen und Nachweise

ORD-Eintrag
ord-89145b683fe949b1ac2ffea1169a32ad
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06914062B2

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