Carbon Dioxide → 1-Isopropyl-1H-1,2,4-triazole-5-carboxylic acid

HRID 244634Notes

Reaction equation

HRID 244634 reaction equation
[CH3:1][CH:2]([N:4]1[CH:8]=[N:7][CH:6]=[N:5]1)[CH3:3].C([Li])CCC.[C:14](=[O:16])=[O:15]>C1COCC1.CCCCCC>[CH3:1][CH:2]([N:4]1[C:8]([C:14]([OH:16])=[O:15])=[N:7][CH:6]=[N:5]1)[CH3:3]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 127624431-(propan-2-yl)-1H-1,2,4-triazoleHCID 178418339Butyllithium

Product 1

HCID 583370201-Isopropyl-1H-1,2,4-triazole-5-carboxylic acidYield 92.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

1-(1-Methylethyl)-1H-1,2,4-triazole (1 g) was dissolved in THF (15 ml) and cooled to −78° C. under nitrogen. A 1.6 M solution of butyllithium in hexane (5.9 ml) was added dropwise. The solution was stirred for 1.5 h at −78° C., then the solution was treated with solid carbon dioxide (2 g). After 30 min at −78° C. the solution was allowed to warm to RT and stirred overnight. The reaction was quenched with water (1 ml), concentrated in vacuo and dried in a vacuum oven for 1 day at 50° C. to give the title compound (1.29 g) as a white solid.

Workup

  1. waitAfter 30 min at −78° C. the solution was allowed
  2. temperatureto warm to RT
  3. stirringstirred overnight
  4. customThe reaction was quenched with water (1 ml)
  5. concentrationconcentrated in vacuo
  6. customdried in a vacuum oven for 1 day at 50° C.

Sources & evidence

ORD record
ord-ef1ee7f52b654ec1a9b88f214e17f4a4
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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