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

HRID 268596ノート

反応式

HRID 268596 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7b10cefd5eda44b68de15df2e3b20ba1
出典データセット
uspto-grants-2008_11
特許番号
US07446117B2

反応ノート

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