Thionyl Chloride → HCID 20506337, compound

HRID 354944Notes

Reaction equation

HRID 354944 reaction equation
[CH2:1]([C:3]1[N:7]([CH2:8][CH2:9]O)[C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[N:4]=1)[CH3:2].S(Cl)([Cl:17])=O>ClC(Cl)Cl>[Cl:17][CH2:9][CH2:8][N:7]1[C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[N:4]=[C:3]1[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 805032HCID 805032, compound

Product 1

HCID 20506337HCID 20506337, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred and refluxing mixture of 7 parts of 2-ethyl-1H-benzimidazole-1-ethanol and 150 parts of trichloromethane are added dropwise 16 parts of sulfinyl chloride. Upon completion, the whole is heated to reflux and stirring is continued for 2 hours at reflux temperature. The reaction mixture is cooled and evaporated. Water is added to the residue and the whole is stirred with activated charcoal. The latter is filtered off and the filtrate is alkalized. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding 1-(2-chloroethyl)-2-ethyl-1H-benzimidazole.

Workup

  1. temperaturerefluxing
  2. temperatureUpon completion, the whole is heated
  3. temperatureto reflux
  4. stirringstirring
  5. temperatureat reflux temperature
  6. temperatureThe reaction mixture is cooled
  7. customevaporated
  8. additionWater is added to the residue
  9. stirringthe whole is stirred with activated charcoal
  10. filtrationThe latter is filtered off
  11. extractionThe product is extracted with trichloromethane
  12. customThe extract is dried
  13. filtrationfiltered
  14. customevaporated
  15. customThe residue is crystallized from 2,2'-oxybispropane
  16. filtrationThe product is filtered off
  17. customdried

Sources & evidence

ORD record
ord-db4d64765eea4e9eb3bc7d69210aabf5
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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