Hydrochloric Acid → sepazonium chloride

HRID 1730219Notes

Reaction equation

HRID 1730219 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-9648fd48b6034aa4a838f8a9b8221a2d
Source dataset
uspto-grants-1976_11
Patent number
US03991202

Reaction notes

Loading…