Thionyl Chloride → Benzimidazol-2-one

HRID 1833614Notes

Reaction equation

HRID 1833614 reaction equation
OCCC[N:5]1[C:9]2[CH:10]=[CH:11][C:12](C(F)(F)F)=[CH:13][C:8]=2[NH:7][C:6]1=[O:18].S(Cl)(Cl)=O>ClC(Cl)Cl>[N:5]1[C:6](=[O:18])[N:7]=[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12

Participants

4

Reactant 2

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

Product 1

HCID 162542Benzimidazol-2-one

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 a 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. temperatureAfter cooling
  4. customthe reaction mixture is evaporated
  5. customthe residue is crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-f22e9ce75c7940de90e8bd3aaa3cae3b
Source dataset
uspto-grants-1978_01
Patent number
US04066772

Reaction notes

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