Thionyl Chloride → HCID 21424806, compound

HRID 258831Notes

Reaction equation

HRID 258831 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]O)[C:6]=2[CH:14]=1.S(Cl)([Cl:17])=O>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][Cl:17])[C:6]=2[CH:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21424809HCID 21424809, compound

Product 1

HCID 21424806HCID 21424806, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 13 parts of 6-chloro-1,3-dihydro-1-(2-hydroxyethyl)-2H-benzimidazol-2-one in 225 parts of trichloromethane are added dropwise 32 parts of sulfinyl chloride. Upon completion, stirring is continued for 7 hours at reflux temperature. The reaction mixture is evaporated and the residue is triturated in water. The solid product is filtered off and crystallized from a mixture of 2-propanol and 2,2'-oxybispropane. It is filtered off again and dried, yielding 5 parts (35.5%) of 6-chloro-1-(2-chloroethyl)-1,3-dihydro-2H-benzimidazol-2-one; mp. 164° C.

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture is evaporated
  3. customthe residue is triturated in water
  4. filtrationThe solid product is filtered off
  5. customcrystallized from a mixture of 2-propanol and 2,2'-oxybispropane
  6. filtrationIt is filtered off again
  7. customdried

Sources & evidence

ORD record
ord-3bf032eb847349059ac19d55cc092832
Source dataset
uspto-grants-1977_07
Patent number
US04035369

Reaction notes

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