Hydrochloric Acid → sepazonium chloride

HRID 328649Notes

Reaction equation

HRID 328649 reaction equation
Cl.[Br-].[Cl:3][C:4]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:5]=1[CH:6]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[Cl:30])[CH2:7][N+:8]1[CH:12]=[CH:11][N:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1>CO>[Cl-:3].[Cl:3][C:4]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:5]=1[CH:6]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[Cl:30])[CH2:7][N+:8]1[CH:12]=[CH:11][N:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86734178HCID 86734178, compound

Product 1

HCID 65336sepazonium chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.2 Mole of gaseous hydrogen chloride is dissolved in 32 parts of methanol and to this solution are added 12 parts of 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-phenethylimidazolium bromide. The resulting mixture is heated slowly to reflux temperature and stirred at reflux for 1.25 hours. The mixture is then cooled and evaporated, and the residue is triturated in n-hexane. The latter is decanted and the residual oil is boiled in methyl ethyl ketone, whereupon the desired product is precipitated as a solid. The latter is filtered off and crystallized from dioxane to obtain a purified 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-phenethylimidazolium chloride product, m.p. 159.5° C.

Workup

  1. temperatureThe resulting mixture is heated slowly
  2. temperatureto reflux temperature
  3. temperatureat reflux for 1.25 hours
  4. temperatureThe mixture is then cooled
  5. customevaporated
  6. customthe residue is triturated in n-hexane
  7. customThe latter is decanted
  8. customis precipitated as a solid
  9. filtrationThe latter is filtered off
  10. customcrystallized from dioxane

Sources & evidence

ORD record
ord-f3f16bbc64224c528fbd42e281fdb374
Source dataset
uspto-grants-1977_04
Patent number
US04017631

Reaction notes

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