p-Toluenesulfonic acid → 2-((2-Chloroanilino)methyl)-2-imidazoline p-toluenesulfonate

Participants

Reaction Steps

The compound 2-((2-chloroanilino)methyl)-2-imidazoline p-toluenesulfonate was prepared using substantially the same procedure described above by heating a mixture of o-chloroanilinoacetonitrile (43.9 g), ethylenediamine p-toluenesulfonate (61.5 g) and 1,2-dichlorobenzene (198 ml). The p-toluenesulfonate salt was hydrolyzed to the free base, i.e., 2-((2-chloroanilino)methyl)-2-imidazoline by slurrying the p-toluenesulfonate salt in water, basifying the slurry and extracting the mixture with CH2Cl2. The methylene chloride was evaporated leaving 38.0 g of the free base. The free base was put in solution in isopropyl alcohol and acidified with hydrochloric acid in isopropyl alcohol which resulted in crystal formation.

Provenance & Evidence