Thionyl Chloride → HCID 20506373, compound

HRID 354923Notes

Reaction equation

HRID 354923 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]([CH2:11][CH2:12][CH2:13]O)[C:8](=[O:15])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:18])=O>ClC(Cl)Cl>[Cl:1][C:2]1[C:10]2[N:9]([CH2:11][CH2:12][CH2:13][Cl:18])[C:8](=[O:15])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 203855604-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one

Product 1

HCID 20506373HCID 20506373, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 5 parts of 4-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one and 75 parts of trichloromethane are added dropwise 8 parts of sulfinyl chloride. Upon completion, stirring is continued for 3 hours at reflux temperature. The reaction mixture is cooled and evaporated. The residue is stirred in a small amount of 4-methyl-2-pentanone. The product is filtered off and dried, yielding 4-chloro-3-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one.

Workup

  1. temperatureat reflux temperature
  2. temperatureThe reaction mixture is cooled
  3. customevaporated
  4. stirringThe residue is stirred in a small amount of 4-methyl-2-pentanone
  5. filtrationThe product is filtered off
  6. customdried

Sources & evidence

ORD record
ord-b1f2bcffb4fd4ad7bdd9327319471a84
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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