Thionyl Chloride → Benzimidazole, 1-(4-chlorobutyl)-

HRID 46893

Reaktionsgleichung

Reaktionsgleichung von HRID 46893
[N:1]1([CH2:10][CH2:11][CH2:12][CH2:13]O)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.S(Cl)([Cl:17])=O>ClC(Cl)Cl>[Cl:17][CH2:13][CH2:12][CH2:11][CH2:10][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 205063231h-Benzimidazole-1-butanol

Produkt 1

HCID 583170Benzimidazole, 1-(4-chlorobutyl)-Ausbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a stirred mixture of 50 parts of 1H-benzimidazol-1-butanol and 375 parts of trichloromethane are added dropwise 35.2 parts of sulfinyl chloride. Upon completion, stirring is continued for 3 hours at reflux temperature. The reaction mixture is evaporated. The residue is taken up in trichloromethane. The whole is washed with ammonium hydroxide and the solvent is evaporated. The residue is purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated, yielding 22 parts (45%) of 1-(4-chlorobutyl)-1H-benzimidazole as an oily residue.

Aufarbeitung

  1. temperatureat reflux temperature
  2. customThe reaction mixture is evaporated
  3. washThe whole is washed with ammonium hydroxide
  4. customthe solvent is evaporated
  5. customThe residue is purified by column-chromatography over silica gel
  6. customThe pure fractions are collected
  7. customthe eluent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ce402052276644ef866f0664ea4fdbd2
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175129

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