Thionyl Chloride → HCID 20506322, compound

HRID 1413468Notes

Reaction equation

HRID 1413468 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]([CH2:11][CH2:12][CH2:13]O)[C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[CH:3]=1.S(Cl)([Cl:19])=O>ClC(Cl)Cl>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]([CH2:11][CH2:12][CH2:13][Cl:19])[C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 205063725-chloro-2-ethyl-1H-benzimidazole-1-propanol

Product 1

HCID 20506322HCID 20506322, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 4 parts of 5-chloro-2-ethyl-1H-benzimidazole-1-propanol and 150 parts of trichloromethane are added dropwise 9.6 parts of sulfinyl chloride. Upon completion, the whole is heated to reflux and stirring is continued for 2 hours at reflux temperature. The reaction mixture is cooled and evaporated. The residue is taken up in water and stirred with activated charcoal. The latter is filtered off and the filtrate is alkalized with ammonium hydroxide. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated, yielding 5-chloro-1-(3-chloropropyl)-2-ethyl-1H-benzimidazole.

Workup

  1. temperatureUpon completion, the whole is heated
  2. temperatureto reflux
  3. temperatureat reflux temperature
  4. temperatureThe reaction mixture is cooled
  5. customevaporated
  6. stirringstirred with activated charcoal
  7. filtrationThe latter is filtered off
  8. extractionThe product is extracted with trichloromethane
  9. customThe extract is dried
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-564a94edfd444a28a1ad0327aee0162a
Source dataset
uspto-grants-1981_02
Patent number
US04250176

Reaction notes

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