Chloroacetyl chloride → 2-Chloro-N-(3-fluoro-pyridin-4-yl)-acetamide

HRID 2192386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192386
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].C(N(CC)CC)C.[Cl:16][CH2:17][C:18](Cl)=[O:19]>ClCCl>[Cl:16][CH2:17][C:18]([NH:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[F:1])=[O:19]

Komponenten

5

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 8171224-Amino-3-fluoropyridine

Produkt 1

HCID 595037592-Chloro-N-(3-fluoro-pyridin-4-yl)-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-fluoro-pyridin-4-ylamine (0.2 g) in dry dichloromethane (2 mL) under nitrogen at 0° C. was treated with triethylamine (0.28 mL) followed by slow addition of chloroacetyl chloride (0.16 mL). The reaction mixture was allowed to warm up to room temperature. After 2 h, the mixture was partitioned between dichloromethane and water The phases were separated and the aqueous layer was extracted with dichloromethane (×2). The combined organic layer was washed with brine, dried over sodium sulphate, filtered and concentrated to give the crude product which was purified by silica gel chromatography eluting with 0-100% EtOAc/cyclohexane. The relevant fractions were combined and evaporated to give the title compound (0.11 g) as a pink solid.

Aufarbeitung

  1. customthe mixture was partitioned between dichloromethane and water The phases
  2. customwere separated
  3. extractionthe aqueous layer was extracted with dichloromethane (×2)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product which
  9. customwas purified by silica gel chromatography
  10. washeluting with 0-100% EtOAc/cyclohexane
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ae5256a72c1b4a959f450ab91dcab968
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329729B2

Notizen zur Reaktion

Wird geladen…