Thionyl Chloride → HCID 20506322, compound

HRID 2050255Notes

Reaction equation

HRID 2050255 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-b01c9ff475de4271829d4d5b4c1e6cd2
Source dataset
uspto-grants-1980_04
Patent number
US04200641

Reaction notes

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