Reaction #55096

Reaction equation

4-hydroxymethyl-5-methylimidazole hydrochloride

cysteamine hydrochloride

→

4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole dihydrochloride

Yield 164.7%

Solvents

isopropyl alcohol

hydrochloric acid

Conditions

Workup

1. 1
   Temperatureunder reflux for 17 hours
2. 2
   ConcentrationConcentration
3. 3
   Otherfollowed by re-evaporation with water
4. 4
   Otherafforded a residue which
5. 5
   Concentrationconcentrated to low bulk
6. 6
   Temperaturecooled

Procedure

A solution of 4-hydroxymethyl-5-methylimidazole hydrochloride (30.0 g.) and cysteamine hydrochloride (23.0 g.) in concentrated aqueous hydrochloric acid (450 ml.) was heated under reflux for 17 hours. Concentration followed by re-evaporation with water afforded a residue which was dissolved in isopropyl alcohol, concentrated to low bulk and cooled to afford 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole dihydrochloride (40.6 g.), m.p. 185°-191°.

Source