Thionyl Chloride → 5-(3-chloropropyl)-1-(alpha-ethoxycarbonyl-p-cyanobenzyl)-1H-imidazole hydrochloride

HRID 477995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 477995
S(Cl)([Cl:3])=O.[CH2:5]([O:7][C:8]([CH:10]([N:19]1[C:23]([CH2:24][CH2:25][CH2:26]O)=[CH:22][N:21]=[CH:20]1)[C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)=[O:9])[CH3:6]>C(Cl)Cl>[ClH:3].[Cl:3][CH2:26][CH2:25][CH2:24][C:23]1[N:19]([CH:10]([C:8]([O:7][CH2:5][CH3:6])=[O:9])[C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[CH:20]=[N:21][CH:22]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 199304171-(alpha-ethoxycarbonyl-p-cyanobenzyl)-1H-imidazole-5-propanol

Produkt 1

HCID 199304155-(3-chloropropyl)-1-(alpha-ethoxycarbonyl-p-cyanobenzyl)-1H-imidazole hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5.75 g of thionylchloride in 80 ml of methylene chloride is added 8.4 g of 1-(α-ethoxycarbonyl-p-cyanobenzyl)-1H-imidazole-5-propanol as a solid in portions. When addition is complete, the solution is refluxed for 1.5 h, cooled in ice and filtered to obtain 5-(3-chloropropyl)-1-(α-ethoxycarbonyl-p-cyanobenzyl)-1H-imidazole hydrochloride. The salt is partitioned between methylene chloride and saturated sodium bicarbonate. The organic extracts are washed with water, dried over sodium sulfate and evaporated to yield the free base.

Aufarbeitung

  1. additionWhen addition
  2. temperaturethe solution is refluxed for 1.5 h
  3. temperaturecooled in ice
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-fbc9eb0c642c46df86fbef6d7a30491a
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04889861

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