Ammonium Chloride → 1-(1-Isopropyl-1H-1,2,4-triazol-5-YL)ethanone

HRID 1498255Notes

Reaction equation

HRID 1498255 reaction equation
[CH:1]([N:4]1[CH:8]=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].C([Li])CCC.[CH3:14][C:15](N(C)C)=[O:16].[Cl-].[NH4+]>C1COCC1>[CH:1]([N:4]1[C:8]([C:15](=[O:16])[CH3:14])=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 127624431-(propan-2-yl)-1H-1,2,4-triazoleHCID 178418339Butyllithium

Product 1

HCID 149783391-(1-Isopropyl-1H-1,2,4-triazol-5-YL)ethanoneYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-isopropyl-1H-[1,2,4]triazole (33 g, 300 mmol) in THF at −10° C. was added n-butyllithium (145 mL, 2.5M, 360 mmol) dropwise over 45 min, and then the mixture stirred at 0° C. for 30 min. DMA (35 mL) was added, the mixture allowed to warm to RT and stirred for 1 h. The resultant suspension was treated with saturated aqueous ammonium chloride (300 mL). The aqueous phase was extracted with ethyl acetate and the combined organic extracts dried (Na2SO4), filtered and concentrated in vacuo to give 1-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-ethanone as a pale orange oil (40.1 g, 87%). 1H NMR δ (ppm) (CDCl3): 7.93 (1 H, s), 5.58-5.46 (1 H, m), 2.72 (3 H, d, J=0.78 Hz), 1.49 (6 H, dd, J=6.61, 0.78 Hz).

Workup

  1. temperatureto warm to RT
  2. stirringstirred for 1 h
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe combined organic extracts dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a8200dea1404de0b2b5fa2e4555ea45
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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