Thionyl Chloride → HCID 20506324, compound

HRID 354932Notes

Reaction equation

HRID 354932 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][CH2:11][CH2:12]O)[C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1.S(Cl)([Cl:18])=O>ClC(Cl)Cl>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][CH2:11][CH2:12][Cl:18])[C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 205063575-chloro-2-methyl-1H-benzimidazole-1-propanol

Product 1

HCID 20506324HCID 20506324, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 6.5 parts of 5-chloro-2-methyl-1H-benzimidazole-1-propanol and 120 parts of trichloromethane are added dropwise 12 parts of sulfinyl chloride. Upon completion, the whole is heated to reflux and stirring is continued for 3 hours at reflux temperature. The reaction mixture is cooled and evaporated. Water is added to the residue and the mixture is treated 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. The residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding 5-chloro-1-(3-chloropropyl)-2-methyl-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. additionWater is added to the residue
  7. additionthe mixture is treated with activated charcoal
  8. filtrationThe latter is filtered off
  9. extractionThe product is extracted with trichloromethane
  10. customThe extract is dried
  11. filtrationfiltered
  12. customevaporated
  13. customThe residue is crystallized from 2,2'-oxybispropane
  14. filtrationThe product is filtered off
  15. customdried

Sources & evidence

ORD record
ord-ec96dff8fca540d0b365ecd2995195ab
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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