Dimethylformamide → 1-Ethyl-1H-1,2,4-triazole-5-carbaldehyde

HRID 268596Notes

Reaction equation

HRID 268596 reaction equation
[CH2:1]([N:3]1[CH:7]=[N:6][CH:5]=[N:4]1)[CH3:2].CN(C)CCN(C)C.C([Li])CCC.CN([CH:24]=[O:25])C.C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:1]([N:3]1[C:7]([CH:24]=[O:25])=[N:6][CH:5]=[N:4]1)[CH3:2]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 516892Sodium BicarbonateHCID 5193051-Ethyl-1,2,4-triazoleHCID 178418339Butyllithium

Product 1

HCID 280649451-Ethyl-1H-1,2,4-triazole-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-ethyl-1H-1,2,4-triazole (9.9 g, 0.10 mol) and N,N,N′,N′-tetramethylethylenediamine (15 mL) in THF (60 mL) at −78° C. was added n-butyllithium (64 mL of a 1.6M solution in hexanes, 0.10 mol). After stirring for 2 hours, DMF (8.7 mL, 0.11 mol) was added, the reaction allowed to warm to room temperature and stirred for 14 hours before being poured into saturated aqueous sodium bicarbonate solution (300 mL). The mixture was extracted with dichloromethane (3×150 mL) and the combined organics dried over sodium sulfate, filtered and concentrated to give the title compound (>12 g) which also contained unreacted starting material 1H-NMR (CDCl3) δ 1.48 (3H, t, J=7 Hz), 4.63 (2H, q, 7 Hz), 8.03 (1H, s), 10.04 (s, 1H).

Workup

  1. stirringstirred for 14 hours
  2. extractionThe mixture was extracted with dichloromethane (3×150 mL)
  3. dry with materialthe combined organics dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7b10cefd5eda44b68de15df2e3b20ba1
Source dataset
uspto-grants-2008_11
Patent number
US07446117B2

Reaction notes

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