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

HRID 2420332Notes

Reaction equation

HRID 2420332 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 50 parts of 1H-benzimidazole-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.

Workup

  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

Sources & evidence

ORD record
ord-b20aec02d82e4917b1fbd6a0c8dc26a7
Source dataset
uspto-grants-1978_08
Patent number
US04110333

Reaction notes

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