Chloroacetyl chloride → 2-chloro-1-(4-(5-(1-methyl-1H-1,2,4-triazol-3-yl)pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone

HRID 1020963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020963
[OH-].[Na+].[Cl:3][CH2:4][C:5](Cl)=[O:6].Cl.Cl.[CH3:10][N:11]1[CH:15]=[N:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=3)=[N:20][CH:21]=2)=[N:12]1>C(Cl)Cl.O>[Cl:3][CH2:4][C:5]([N:25]1[CH2:24][CH2:23][C:22]([C:19]2[CH:18]=[CH:17][C:16]([C:13]3[N:14]=[CH:15][N:11]([CH3:10])[N:12]=3)=[CH:21][N:20]=2)=[CH:27][CH2:26]1)=[O:6]

Komponenten

6

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 673440865-(1-methyl-1H-1,2,4-triazol-3-yl)-2-(1,2,3,6-tetrahydropyridin-4-yl)pyridine dihydrochloride

Produkt 1

HCID 583719992-chloro-1-(4-(5-(1-methyl-1H-1,2,4-triazol-3-yl)pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)ethanoneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Added 1N NaOH (50 ml, 50 mmol) and Chloroacetyl chloride (3 ml, 37.7 mmol) in CH2Cl2 (50 ml) dropwise to a solution of 5-(1-methyl-1H-1,2,4-triazol-3-yl)-2-(1,2,3,6-tetrahydropyridin-4-yl)pyridine dihydrochloride (5BX) (1 g, 3.60 mmol) in CH2Cl2 (50 ml at 0° C., maintaining pH at >12. Mixture was stirred for 2 hours at 0° C., then reaction was diluted with CH2Cl2 (200 ml) and H2O (100 ml). The organic layer was separated, washed with H2O (50 ml), dried (Na2SO4), filtered and solvent evaporated yielding title product as a white solid (1.1 g, 100%) MS (MH, 318)

Aufarbeitung

  1. temperaturemaintaining pH at >12
  2. customreaction
  3. customThe organic layer was separated
  4. washwashed with H2O (50 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customsolvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-a4236ca36aa54877b96952a97071e7ae
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716483B2

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