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

HRID 856643Notes

Reaction equation

HRID 856643 reaction equation
[N+]([O-])(O)=O.N([O-])=O.[Na+].[OH:9][CH2:10][C:11]1[N:15]([CH2:16][CH3:17])[C:14](S)=[N:13][N:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH2:16]([N:15]1[CH:14]=[N:13][N:12]=[C:11]1[CH2:10][OH:9])[CH3:17]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 178462988HCID 178462988, compound

Product 1

HCID 229386114-Ethyl-4H-1,2,4-triazole-3-methanolYield 76.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 90% nitric acid (15 ml) and water (22 ml) was added sodium nitrite (0.06 g) and then 3-hydroxymethyl-5-mercapto-4-ethyl-4H-1,2,4-triazole (7.5 g) was slowly added for 0.5 hours at 45° C. After allowing the mixture to be cooled to room temperature, 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, and the obtained residue was separated and purified by column chromatography (ethanol:ethyl acetate 2:1), to give 4-ethyl-3-hydroxymethyl-4H-1,2,4-triazole (4.60 g) as brown oil.

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
  6. customthe obtained residue was separated
  7. custompurified by column chromatography (ethanol:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-9bde39f0164e4e79b0adf9981279ccc0
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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