Sodium Sulfite → 1-((4-Hydrazinylphenyl)methyl)-1H-1,2,4-triazole hydrochloride (1:2)

HRID 1180098Notes

Reaction equation

HRID 1180098 reaction equation
[ClH:1].[N:2]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH:6]=[N:5][CH:4]=[N:3]1.[N:15]([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>O.Cl>[ClH:1].[N:2]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][NH2:15])=[CH:10][CH:9]=2)[CH:6]=[N:5][CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 24437Sodium SulfiteHCID 117012794-(1H-1,2,4-Triazol-1-ylmethyl)benzenamine hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 233746011-((4-Hydrazinylphenyl)methyl)-1H-1,2,4-triazole hydrochloride (1:2)

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent3×

Procedure

To a solution of 1.5 g (7.1 mmoles) of 4-(1,2,4-triazol-1-ylmethyl)phenylamine hydrochloride in 3.75 ml of water and 6.3 ml of concentrated HCl, cooled to 0° C., was added slowly a solution of 0.5 g (7.2 mmoles) of sodium nitrite in 2.6 ml of water, keeping the temperature below 0° C. The mixture was stirred at this temperature for 15 minutes. Once this time had elapsed the solution of the diazonium salt was added rapidly to a solution of 5.37 g (42.6 mmoles) of sodium sulphite in 19 ml of water precooled to 0° C. under nitrogen atmosphere. The red solution was stirred at 0° C. for 10 minutes and then left to reach 65° C. in 1 hour. It was stirred at 65° C. for 30 minutes, and 5 ml of concentrated HCl were then added. The mixture was stirred at the same temperature under nitrogen atmosphere for 3 hours and then left to cool to room temperature.

Workup

  1. customthe temperature below 0° C
  2. customprecooled to 0° C. under nitrogen atmosphere
  3. stirringThe red solution was stirred at 0° C. for 10 minutes
  4. waitleft
  5. waitto reach 65° C. in 1 hour
  6. stirringIt was stirred at 65° C. for 30 minutes
  7. stirringThe mixture was stirred at the same temperature under nitrogen atmosphere for 3 hours
  8. waitleft

Sources & evidence

ORD record
ord-987439bbfbd84a2c9b87a3f5b8c7cac7
Source dataset
uspto-grants-2007_10
Patent number
US07279581B2

Reaction notes

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