Pyridine → HCID 69671260, Verbindung

HRID 529875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 529875
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([NH:12][CH:13]([CH:15]([CH3:17])[CH3:16])[CH3:14])=[CH:9][C:10]#[N:11].[CH:18]1([CH2:21][C:22](Cl)=[O:23])C[CH2:19]1.N1C=CC=CC=1>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([NH:12][CH:13]([CH:15]([CH3:17])[CH3:16])[CH3:14])=[C:9]([C:22](=[O:23])[CH2:21][CH2:18][CH3:19])[C:10]#[N:11]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 143262682-Cyclopropylacetyl chlorideHCID 69671093HCID 69671093, Verbindung

Produkt 1

HCID 69671260HCID 69671260, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3-(2-chlorophenyl)-3-[(3-methylbutan-2-yl)amino]acrylonitrile (1 g, 4.02 mmol, 1 eq.) in 1,2-dichloroethane (2 ml) were added cyclopropylacetyl chloride (1.71 g, 16.08 mmol, 4 eq.) and pyridine (1.58 g, 20.1 mmol, Seq.) and the solution was heated to 80° C. for 8 h. The reaction was quenched with 1N aq. HCl (20 ml) and extracted with ethylacetate. The organic layers were combined and washed with 1N aq. NaOH (20 ml), dired over MgSO4 and concentration under vacuum. The residual oil was subjected to column chromatography to give 2-{(2-chlorophenyl)[(3-methylbutan-2-yl)amino]methylene}-3-oxohexanenitrile (1.012 g, 75% yield).

Aufarbeitung

  1. customThe reaction was quenched with 1N aq. HCl (20 ml)
  2. extractionextracted with ethylacetate
  3. washwashed with 1N aq. NaOH (20 ml), dired over MgSO4 and concentration under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-571ec33ce857474d9dc383940599cbad
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09351489B2

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