Thionyl Chloride → 5-chloro-1-(3-chloropropyl)-2-cyclohexyl-1H-benzimidazole hydrochloride

HRID 354936Notes

Reaction equation

HRID 354936 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]([CH2:15][CH2:16][CH2:17]O)[C:7]([CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1.S(Cl)([Cl:23])=O>ClC(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]([CH2:15][CH2:16][CH2:17][Cl:23])[C:7]([CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 131056175-chloro-2-cyclohexyl-1H-benzimidazole-1-propanol

Product 1

HCID 205063335-chloro-1-(3-chloropropyl)-2-cyclohexyl-1H-benzimidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 21 parts of 5-chloro-2-cyclohexyl-1H-benzimidazole-1-propanol in 225 parts of trichloromethane are added dropwise 40 parts of sulfinyl chloride (exothermic reaction). Upon completion, stirring is continued for 2 hours at reflux temperature. The reaction mixture is evaporated and the residue is dissolved in boiling water. The solution is treated with activated charcoal. The latter is filtered off till a clear filtrate is obtained. After cooling in an ice-bath, the precipitated product is filtered off and dried, yielding 5-chloro-1-(3-chloropropyl)-2-cyclohexyl-1H-benzimidazole hydrochloride; mp. 211.7° C.

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture is evaporated
  3. dissolutionthe residue is dissolved
  4. additionThe solution is treated with activated charcoal
  5. filtrationThe latter is filtered off till a clear filtrate
  6. customis obtained
  7. temperatureAfter cooling in an ice-bath
  8. filtrationthe precipitated product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-f42691a8257148a4a46e50549065c71c
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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