Methanol → trans-3-[2-(7-Chloroquinolin-2-yl)ethenyl]benzyl chloride

HRID 1198540

Reaktionsgleichung

Reaktionsgleichung von HRID 1198540
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12](/[CH:16]=[CH:17]/[C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[CH2:21]O)=[N:13]2)=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+].CO>ClCCCl>[Cl:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12](/[CH:16]=[CH:17]/[C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[CH2:21][Cl:3])=[N:13]2)=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 10827738trans-3-[2-(7-Chloroquinolin-2-yl)ethenyl]benzyl alcohol

Produkt 1

HCID 19369489trans-3-[2-(7-Chloroquinolin-2-yl)ethenyl]benzyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Thionyl chloride (3.6 ml., 49.3 mmol) was added rapidly to a stirred solution of 3-[2(E)-(7-chloroquinolin-2-yl)ethenyl]benzyl alcohol (Example 6a part (ii)) (11.7 g, 39.5 mmol) in 1,2-dichloroethane (300 ml) at 50° C. giving an immediate yellow precipitate. The mixture was stirred for 1 hour and cooled to room temperature then the mixture was shaken with saturated sodium bicarbonate solution (400 ml) and methanol (50 ml) to give two clear phases. The aqueous phase was extracted with dichloromethane and the combined solvent phase was dried and evaporated.

Aufarbeitung

  1. customgiving an immediate yellow precipitate
  2. customto give two clear phases
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. customthe combined solvent phase was dried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9828fbef99d24a878dc0b78475db45fd
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05281593

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