Thionyl Chloride → 1-(3-chloropropyl)-1,3-dihydro-5-(trifluoromethyl)-2H-benzimidazol-2-one

HRID 1704530Notes

Reaction equation

HRID 1704530 reaction equation
O[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]([F:17])([F:16])[F:15])=[CH:13][C:8]=2[NH:7][C:6]1=[O:18].S(Cl)([Cl:21])=O>ClC(Cl)Cl>[Cl:21][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]([F:17])([F:16])[F:15])=[CH:13][C:8]=2[NH:7][C:6]1=[O:18]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 203856341,3-dihydro-1-(3-hydroxypropyl)-5-(trifluoromethyl)-2H-benzimidazol-2-one

Product 1

HCID 203855741-(3-chloropropyl)-1,3-dihydro-5-(trifluoromethyl)-2H-benzimidazol-2-oneYield 56%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 23 parts of 1,3-dihydro-1-(3-hydroxypropyl)-5-(trifluoromethyl)-2H-benzimidazol-2-one in 150 parts of trichloromethane are added dropwise 32 parts of sulfinyl chloride. Upon completion, the whole is heated to reflux and stirring is continued for 1 hour at reflux temperature. After cooling, the reaction mixture is evaporated and the residue is crystallized from 2,2'-oxybispropane, yielding 14 parts (56%) of 1-(3-chloropropyl)-1,3-dihydro-5-(trifluoromethyl)-2H-benzimidazol-2-one.

Workup

  1. temperatureUpon completion, the whole is heated
  2. temperatureto reflux
  3. temperatureat reflux temperature
  4. temperatureAfter cooling
  5. customthe reaction mixture is evaporated
  6. customthe residue is crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-7171b755a2d242f8b4a292a703c492e0
Source dataset
uspto-grants-1978_11
Patent number
US04126688

Reaction notes

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