Cysteamine Hydrochloride → 3-(2-Aminoethyl)-4-methyl-1,2,4-triazole dihydrobromide

HRID 972631Notes

Reaction equation

HRID 972631 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][N:4]=[C:3]1[CH2:7][Br:8].[CH3:9][N:10]1C=NN=C1CO.Cl.NCCS>Br>[BrH:8].[BrH:8].[NH2:10][CH2:9][CH2:7][C:3]1[N:2]([CH3:1])[CH:6]=[N:5][N:4]=1

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 15707893(4-methyl-4H-1,2,4-triazol-3-yl)methanolHCID 205578583-(Bromomethyl)-4-methyl-4H-1,2,4-triazole

Product 1

HCID 205577863-(2-Aminoethyl)-4-methyl-1,2,4-triazole dihydrobromide

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent2×

Procedure

The thione (44 g.) was desulphurised by slow addition to a solution prepared from nitric acid (75 ml.), water (150 ml.) and sodium nitrite (1.5 g.) at 15°-20°. Following subsequent basification with sodium carbonate and concentration, the residue was extracted with ethanolether 1:1 and distilled to afford 3-ethoxymethyl-4-methyl-1,2,4-triazole (30 g.), b.p. 154°-156°/0.05 mm. The above compound (15 g.) dissolved in 48% aqueous hydrobromic acid (150 ml.) was heated under reflux for 24 hours, concentrated to dryness and the residue obtained (a mixture of 4-methyl-3-bromomethyl-1,2,4-triazole and 4-methyl-3-hydroxymethyl-1,2,4-triazole) was used directly in the reaction with cysteamine hydrochloride and hydrobromic acid as described in Example 1 (i)(a) to give 3-(2-aminoethyl)-4-methyl-1,2,4-triazole dihydrobromide, m.p. 175°-177°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. concentrationconcentrated to dryness
  4. customthe residue obtained (

Sources & evidence

ORD record
ord-9a4d64a564494e5893d930045a9b92b9
Source dataset
uspto-grants-1977_10
Patent number
US04053473

Reaction notes

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