Thionyl Chloride → 1-Benzyl-4-chloro-5-(chloromethyl)-2(4-nitrophenyl)-imidazole

HRID 896946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896946
S(Cl)([Cl:3])=O.[CH2:5]([N:12]1[C:16]([CH2:17]O)=[C:15]([Cl:19])[N:14]=[C:13]1[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)(Cl)Cl>[CH2:5]([N:12]1[C:16]([CH2:17][Cl:3])=[C:15]([Cl:19])[N:14]=[C:13]1[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 15088539(1-benzyl-4-chloro-2-(4-nitrophenyl)-1H-imidazol-5-yl)methanol

Produkt 1

HCID 223457251-Benzyl-4-chloro-5-(chloromethyl)-2(4-nitrophenyl)-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Thionyl chloride (0.90 ml, 1.48 g, 12.4 mmol) was added dropwise to a stirred suspension of 1-benzyl-4-chloro-5-(hydroxymethyl)-2(4-nitrophenyl)imidazole (18.5 g, 5.4 mmole) in chloroform (15 ml) at room temperature. The brown solution was stirred for 2.5 hours then evaporated to dryness. Toluene (12 ml) was added to the residue and evaporated to dryness. The residue was dissolved in chloroform (20 ml) and used in the next step for introduction of the cyano functional group.

Aufarbeitung

  1. customthen evaporated to dryness
  2. additionToluene (12 ml) was added to the residue
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in chloroform (20 ml)

Quellen und Nachweise

ORD-Eintrag
ord-aea224c8f7c4441386cb5c1a4fd77751
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921525B2

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