Sodium Hydroxide → 1H-Pyrrole-2-carboxylic acid, 4-chloro-3,5-dimethyl, ethyl ester

HRID 1948345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948345
[Cl:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:14]=[C:13]([CH3:15])[NH:12][C:11]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[OH-].[Na+]>C(Cl)(Cl)Cl.CO>[Cl:1][C:14]1[C:10]([CH3:9])=[C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:12][C:13]=1[CH3:15]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 1374771H-Pyrrole-2-carboxylic acid, 3,5-dimethyl-, ethyl ester

Produkt 1

HCID 1435841H-Pyrrole-2-carboxylic acid, 4-chloro-3,5-dimethyl, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

N-Chlorosuccinimide (1.77 g, 13.25 mmol) was added to a solution of ethyl 3,5-dimethyl-2-pyrrole carboxylate (2.11 g, 12.62 mmol) in chloroform (45 mL). The reaction mixture was stirred at room temperature for 24 h and then poured into 2 N NaOH. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a crude solid. The crude solid was dissolved in hot MeOH, cooled to room temperature, and the precipitate was collected by filtration (493 mg, 19%). MS (ES) MH+: 174 for C9H12ClNO2.

Aufarbeitung

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a crude solid
  6. temperaturecooled to room temperature
  7. filtrationthe precipitate was collected by filtration (493 mg, 19%)

Quellen und Nachweise

ORD-Eintrag
ord-ac47a4fc4fe9492e951f6c748de6375d
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399489B2

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