Nitric Acid → 3-(2-Aminoethyl)-4-methyl-1,2,4-triazole dihydrobromide

HRID 2163915Notes

Reaction equation

HRID 2163915 reaction equation
[N+]([O-])(O)=O.[N+]([O-])([O-])=O.[Na+].[CH3:10][N:11]1[CH:15]=[N:14][N:13]=[C:12]1[CH2:16][Br:17].[CH3:18][N:19]1C=NN=C1CO.Cl.NCCS>Br.O>[BrH:17].[BrH:17].[NH2:19][CH2:18][CH2:16][C:12]1[N:11]([CH3:10])[CH:15]=[N:14][N:13]=1

Participants

8

Reactant 5

HCID 944Nitric AcidHCID 9082Cysteamine HydrochlorideHCID 24268Sodium NitrateHCID 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 2

HCID 260Hydrogen BromideSolvent2×HCID 962WaterSolvent

Procedure

The thione (44 g.) was desulphurised by slow addition to a solution prepared from nitric acid (75 ml.), water (150 ml.) and sodium nitrate (1.5 g.) at 15°-20°. Following subsequent basification with sodium carbonate and concentration, the residue was extracted with ethanolether 1 l and distilled to afford 3-ethoxymethyl-4-methyl-1,2,4-triazle (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. concentrationwith sodium carbonate and concentration
  2. extractionthe residue was extracted with ethanolether 1 l
  3. distillationdistilled
  4. customto afford 3-ethoxymethyl-4-methyl-1,2,4-triazle (30 g.)
  5. temperaturewas heated
  6. temperatureunder reflux for 24 hours
  7. concentrationconcentrated to dryness
  8. customthe residue obtained (

Sources & evidence

ORD record
ord-d69b82908ebd49ccbfe98674cb772364
Source dataset
uspto-grants-1979_01
Patent number
US04137234

Reaction notes

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