Thionyl Chloride → Benzimidazole

HRID 1413471Notes

Reaction equation

HRID 1413471 reaction equation
C1(C[C:8]2[N:12](CCCO)[C:11]3[CH:17]=[CH:18][CH:19]=[CH:20][C:10]=3[N:9]=2)C=CC=CC=1.S(Cl)(Cl)=O>ClC(Cl)Cl>[NH:9]1[C:10]2[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=2[N:12]=[CH:8]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20506306HCID 20506306, compound

Product 1

HCID 5798Benzimidazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 40 parts of 2-(phenylmethyl)-1H-benzimidazole-1-propanol and 225 parts of trichloromethane are added dropwise 30 parts of sulfinyl chloride. Upon completion, stirring is continued for 4 hours at reflux temperature. The reaction mixture is evaporated and the residue is boiled in water. The solution is filtered over hyflo 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 a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane. The product is filtered off and dried, yielding 1-(3-chloropropyl)-2-phenylmethyl)-1H-benzimidazole; mp. 112° C.

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture is evaporated
  3. filtrationThe solution is filtered over hyflo
  4. extractionThe product is extracted with trichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane
  9. filtrationThe product is filtered off
  10. customdried

Sources & evidence

ORD record
ord-98ec76e0f66b42d2853f83983e461ee6
Source dataset
uspto-grants-1981_02
Patent number
US04250176

Reaction notes

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