N-bromobutanimide → N-(5-bromo-4-chloropyridin-2-yl)-2,2-dimethylpropanamide

HRID 384679

Reaktionsgleichung

Reaktionsgleichung von HRID 384679
C1C(=O)N([Br:8])C(=O)C1.[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>C(#N)C>[Br:8][C:15]1[C:10]([Cl:9])=[CH:11][C:12]([NH:16][C:17](=[O:22])[C:18]([CH3:19])([CH3:21])[CH3:20])=[N:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 10656204N-(4-Chloropyridin-2-yl)pivalamide

Produkt 1

HCID 59613421N-(5-bromo-4-chloropyridin-2-yl)-2,2-dimethylpropanamideAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

NBS (8.37 g. 47.0 mmol) was added to a solution of N-(4-chloropyridin-2-yl)pivalamide (2.00 g, 9.40 mmol) in dry acetonitrile (20 mL). The resulting suspension was heated for 3 hr and then cooled to r.t. The solvent was removed in vacuo and the crude mixture was diluted with ethyl acetate (100 mL). The organic phase was washed with aqueous NaOH (10%, 2×40 mL), water (40 mL) and dried (MgSO4). The solvent was removed in vacuo and the crude mixture was purified by flash chromatography on silica, eluting with ethyl acetate and hexane (1/9), to give the title compound as a colourless solid (1.82 g, 66%).

Aufarbeitung

  1. temperatureThe resulting suspension was heated for 3 hr
  2. customThe solvent was removed in vacuo
  3. additionthe crude mixture was diluted with ethyl acetate (100 mL)
  4. washThe organic phase was washed with aqueous NaOH (10%, 2×40 mL), water (40 mL)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe crude mixture was purified by flash chromatography on silica
  8. washeluting with ethyl acetate and hexane (1/9)

Quellen und Nachweise

ORD-Eintrag
ord-a0fce03ae79e4e8882d8fa7ee697e6d1
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367658B2

Verknüpfte Notizen

Wird geladen…