Thionyl Chloride → HCID 20506344, compound

HRID 354943Notes

Reaction equation

HRID 354943 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[N:7]([CH2:16][CH2:17][CH2:18]O)[C:6]=2[CH:20]=1.S(Cl)([Cl:23])=O>ClC(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[N:7]([CH2:16][CH2:17][CH2:18][Cl:23])[C:6]=2[CH:20]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20506266HCID 20506266, compound

Product 1

HCID 20506344HCID 20506344, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 50 parts of 6-chloro-2-cyclohexyl-1H-benzimidazole-1-propanol in 375 parts of trichloromethane are added dropwise 60 parts of sulfinyl chloride (exothermic reaction). Upon completion, stirring is continued for 2 hours at reflux temperature. The reaction mixture is evaporated and the semi-solid residue is dissolved in hot water. The solution is stirred with activated charcoal. The latter is filtered hot over hyflo and the filtrate is stirred in an ice-bath. The precipitated product is filtered off and dried, yielding 6-chloro-1-(3-chloropropyl)-2-cyclohexyl-1H-benzimidazole hydrochloride; mp. 227.5° C.

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture is evaporated
  3. dissolutionthe semi-solid residue is dissolved in hot water
  4. stirringThe solution is stirred with activated charcoal
  5. filtrationThe latter is filtered hot over hyflo
  6. stirringthe filtrate is stirred in an ice-bath
  7. filtrationThe precipitated product is filtered off
  8. customdried

Sources & evidence

ORD record
ord-cb35eefaf1ae461e85decca799005eec
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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