Chlorosuccinimide → N-(4,5-Dichloropyridin-2-yl)pivalamide

HRID 323557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 323557
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:11]=1>CC#N>[Cl:9][C:10]1[C:15]([Cl:1])=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:22])[C:18]([CH3:19])([CH3:21])[CH3:20])[CH:11]=1

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 10656204N-(4-Chloropyridin-2-yl)pivalamide

Produkt 1

HCID 10538422N-(4,5-Dichloropyridin-2-yl)pivalamideAusbeute 96,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

N-chloro-succinimide (NCS, 79.45 g, 0.6 mol) was added to a solution of compound 7 (25.8 g, 0.12 mol) in dry CH3CN (300 mL). The resulting suspension was heated at reflux for 2 hours and then cooled to room temperature. After washing with 10% aqueous NaOH (2×150 mL), then water (2×200 mL), the organic phase was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give a solid. This solid was recrystallized from EtOH to give 28.7 g (95%) of compound 8 as a white solid.

Aufarbeitung

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 2 hours
  3. washAfter washing with 10% aqueous NaOH (2×150 mL)
  4. dry with materialwater (2×200 mL), the organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a solid
  8. customThis solid was recrystallized from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-6b628a8eae9d41bea3d9a99d0250dd96
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06214801B1

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