Methane → 6-chloro-1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 1704546Notes

Reaction equation

HRID 1704546 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH2:11][CH2:12][CH2:13]O)[C:6]=2[CH:15]=1.S(Cl)([Cl:18])=O.C>ClC(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH2:11][CH2:12][CH2:13][Cl:18])[C:6]=2[CH:15]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 24386Thionyl ChlorideHCID 203856516-chloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one

Product 1

HCID 203855876-chloro-1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-oneYield 77.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 22.6 parts of 6-chloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one and 300 parts of trichloromethane are added dropwise 32 parts of sulfinyl chloride. Upon completion, stirring is continued for 3 hours at reflux. After stirring with activated charcoal, the reaction mixture is filtered hot over hyflo. The filtrate is evaporated and the residue is dissolved in methylbenzene. The solution is washed a few times with water, dried, filtered and evaporated. The oily residue is triturated in 2,2'-oxybispropane. The solid product is filtered off and dried, yielding 19 parts (77.5%) of 6-chloro-1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one; mp. 122° C.

Workup

  1. temperatureat reflux
  2. filtrationthe reaction mixture is filtered hot over hyflo
  3. customThe filtrate is evaporated
  4. dissolutionthe residue is dissolved in methylbenzene
  5. washThe solution is washed a few times with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe oily residue is triturated in 2,2'-oxybispropane
  10. filtrationThe solid product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-aa528d9060df47a7a9048a043d8d788b
Source dataset
uspto-grants-1978_11
Patent number
US04126688

Reaction notes

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