Thionyl Chloride → 1-benzyl-2-(chloromethyl)-1H-imidazole

HRID 1253030

Reaktionsgleichung

Reaktionsgleichung von HRID 1253030
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:17])=O>>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][Cl:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 24386Thionyl ChlorideHCID 311778(1-benzyl-1H-imidazol-2-yl)methanol

Produkt 1

HCID 7367921-benzyl-2-(chloromethyl)-1H-imidazoleAusbeute 93,5 %

Versuchsvorschrift

A mixture of 10 gm (45 mmole) of N-benzyl-2-hydroxymethylimidazole and 11 gm (92 mmole) of thionyl chloride was stirred at room temperature for 30 minutes before it was heated to reflux for 30 minutes. The excess thionyl chloride was removed under reduced pressure. The resultant residue (10 gm crude) was crystallized from ethanol/ether to obtain 8.7 gm of N-benzyl-2-chloromethylimidazole, m.p. 180°-182° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. customThe excess thionyl chloride was removed under reduced pressure
  4. customThe resultant residue (10 gm crude) was crystallized from ethanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-39fad1f746cd4c8a807fe30658bab454
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04746669

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