Triethylamine → (5-Phenyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-3-yl)methanone

HRID 1904685

Reaktionsgleichung

Reaktionsgleichung von HRID 1904685
[C:1]1([CH:7]2[NH:11][N:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=1>C(Cl)(Cl)Cl>[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([N:11]2[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH:9]=[N:10]2)=[O:27])[CH:22]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 1208415-Phenyl-4,5-dihydro-1H-pyrazole

Produkt 1

HCID 3078467(5-Phenyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-3-yl)methanoneAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 5-phenyl-2-pyrazoline (2.9 g) and triethylamine (4 g) was added dropwise with ice cooling to a suspension of nicotinoyl chloride hydrochloride (4 g) in 20 ml chloroform, the resulting mixture was stirred for 15 minutes, washed with water and concentrated, and the concentrate was purified by silica gel chromatography (chloroform/methanol=100/1), giving 4.3 g (yield: 86%) of pure product. M.p. 100°-102° C.; NMR (CDCl3): 2.9-3.8 (2H, m), 5.61 (1H, dd, J=5, 12 Hz), 7.03 (1H, t, J=2 Hz), 7.31 (5H, s), 7.28 (1H, m), 8.15 (1H, dt, J=8, 2 Hz), 8.68 (1H, dd, J=2, 6 Hz), 9.13(1H, d, J=2 Hz).

Aufarbeitung

  1. washwashed with water
  2. concentrationconcentrated
  3. customthe concentrate was purified by silica gel chromatography (chloroform/methanol=100/1)

Quellen und Nachweise

ORD-Eintrag
ord-6d56b42708264f458ab9c8c2ec6083c0
Quelldatensatz
uspto-grants-1989_06
Patentnummer
US04839376

Verknüpfte Notizen

Wird geladen…