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

HRID 268596노트

반응식

HRID 268596 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7b10cefd5eda44b68de15df2e3b20ba1
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446117B2

반응 노트

불러오는 중…