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Cysteamine Hydrochloride → 2-(((5-Methyl-1H-imidazol-4-yl)methyl)thio)ethylamine dihydrochloride

HRID 26818
Notes
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Reaction equation

HRID 26818 reaction equation
[ClH:1].O[CH2:3][C:4]1[N:5]=[CH:6][NH:7][C:8]=1[CH3:9].Cl.[NH2:11][CH2:12][CH2:13][SH:14]>Cl.C(O)(C)C>[ClH:1].[ClH:1].[CH3:9][C:8]1[N:7]=[CH:6][NH:5][C:4]=1[CH2:3][S:14][CH2:13][CH2:12][NH2:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 9082Cysteamine HydrochlorideHCID 30847074-Methylimidazol-5-ylmethanolhydrochloride

Product 1

HCID 30159992-(((5-Methyl-1H-imidazol-4-yl)methyl)thio)ethylamine dihydrochlorideYield 164.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

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°.

Workup

  1. temperatureunder reflux for 17 hours
  2. concentrationConcentration
  3. customfollowed by re-evaporation with water
  4. customafforded a residue which
  5. concentrationconcentrated to low bulk
  6. temperaturecooled

Sources & evidence

ORD record
ord-2e6aab42d5a84577b0a2369f52c36f5b
Source dataset
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04151288

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes