Thionyl Chloride → HCID 20506327, compound

HRID 2050251Notes

Reaction equation

HRID 2050251 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]([CH2:16][CH2:17][CH2:18]O)[C:7]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:8][C:4]=2[CH:3]=1.S(Cl)([Cl:24])=O>ClC(Cl)Cl>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]([CH2:16][CH2:17][CH2:18][Cl:24])[C:7]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 205062705-chloro-2-(phenylmethyl)-1H-benzimidazole-1-propanol

Product 1

HCID 20506327HCID 20506327, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 45 parts of 5-chloro-2-(phenylmethyl)-1H-benzimidazole-1-propanol and 225 parts of trichloromethane are added dropwise 29.75 parts of sulfinyl chloride. Upon completion, stirring is continued for 6 hours at reflux temperature. The reaction mixture is evaporated and the residue is taken up in water. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 5-chloro-1-(3-chloropropyl)-2-(phenylmethyl)-1H-benzimidazole as a solid residue.

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture is evaporated
  3. extractionThe product is extracted with trichloromethane
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (98:2) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated

Sources & evidence

ORD record
ord-68ce8a319f2841aba687a76ea59a49d3
Source dataset
uspto-grants-1980_04
Patent number
US04200641

Reaction notes

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