Nitric Acid → 4-Propyl-4H-1,2,4-triazole-3-methanol

HRID 856646Notes

Reaction equation

HRID 856646 reaction equation
[N+]([O-])(O)=O.N([O-])=O.[Na+].[OH:9][CH2:10][C:11]1[N:15]([CH2:16][CH2:17][CH3:18])[C:14](S)=[N:13][N:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[OH:9][CH2:10][C:11]1[N:15]([CH2:16][CH2:17][CH3:18])[CH:14]=[N:13][N:12]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 178456617HCID 178456617, compound

Product 1

HCID 229386294-Propyl-4H-1,2,4-triazole-3-methanolYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 90% nitric acid (18 ml) and water (26 ml) was added sodium nitrite (0.07 g) and then 3-hydroxymethyl-5-mercapto-4-propyl-4H-1,2,4-triazole (10 g) was slowly added for 0.5 hours at 45° C. After cooling to room temperature, and sodium carbonate was slowly added thereto to adjust pH to 7 at 0° C. The reaction mixture was concentrated under reduced pressure, methanol was added to the residue, and the precipitates were removed by filtration. The mixture was concentrated under reduced pressure, dichloromethane was added to the residue, the precipitates were removed by filtration, and the filtrate was concentrated to give 3-hydroxymethyl-4-propyl-4H-1,2,4-triazole (5.95 g) as a crude product.

Workup

  1. customto adjust pH to 7 at 0° C
  2. concentrationThe reaction mixture was concentrated under reduced pressure, methanol
  3. additionwas added to the residue
  4. customthe precipitates were removed by filtration
  5. concentrationThe mixture was concentrated under reduced pressure, dichloromethane
  6. additionwas added to the residue
  7. customthe precipitates were removed by filtration
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d6531465c312481f9a67b11d79fb6e36
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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