Ethylenediamine → 1,2-di-[3-(N-vinylformamido)propionamido]ethane

HRID 2384

반응식

HRID 2384 반응식
[CH:1]([N:3]([CH2:6][CH2:7][C:8]([O:10]CC)=O)[CH:4]=[O:5])=[CH2:2].[CH2:13]([NH2:16])[CH2:14][NH2:15].[CH3:17][O-:18].[Na+]>CO>[CH:1]([N:3]([CH2:6][CH2:7][C:8]([NH:15][CH2:14][CH2:13][NH:16][C:8](=[O:10])[CH2:7][CH2:6][N:3]([CH:1]=[CH2:2])[CH:4]=[O:5])=[O:10])[CH:17]=[O:18])=[CH2:2]

참가 물질

5

반응물 3

HCID 3301Ethylenediamine2회HCID 10942334Sodium MethoxideHCID 19690337ethyl 3-(N-vinylformamido)propionate

생성물 1

HCID 196903491,2-di-[3-(N-vinylformamido)propionamido]ethane

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
90 °C

실험 절차

The apparatus of Example 2 was charged with 17.1 grams (0.1 mole) of ethyl 3-(N-vinylformamido)propionate, 3.0 grams (0.05 mole) of ethylenediamine and 0.12 gram of 25% sodium methoxide in methanol solution. The mixture was stirred at 90° C. for 3 hours, after which the ethanol coproduct was removed by distillation at reduced pressure. The mixture was then allowed to cool to room temperature yielding the crude product as a yellow solid. NMR analysis of the reaction mixture indicated nearly complete conversion of the ethylenediamine. The solid was recrystallized from toluene/acetone to give pale yellow crystals of 1,2-di-[3-(N-vinylformamido)propionamido]ethane. 1H NMR (CDCl3) δ, major rotamer: 2.46 (t, 4H, J=6.2 Hz), 3.30 (bs, 4H), 3.86 (t, 4H, J=7.3 Hz), 4.48 (d, 2H, J=8.7 Hz), 4.70 (d, 2H, J=15.8 Hz), 6.54 (d,d, 2H, J=9.1 Hz, J=15.6 Hz), 6.90 (bs, 2H), 8.25 (d, 2Hz, J=5.6 Hz); minor rotamer: most peaks overlapped with peaks of the major rotamer, except, 6.68 (bs, 2H), 7.13 (d,d, 2H, J=9.3 Hz, J=16.3 Hz), 8.14 (d, 2H, J=5.3 H). Major/minor rotamer ratio: 76:24.

후처리

  1. customafter which the ethanol coproduct was removed by distillation at reduced pressure
  2. temperatureto cool to room temperature
  3. customyielding the crude product as a yellow solid
  4. customThe solid was recrystallized from toluene/acetone

출처 및 근거

ORD 기록
ord-d45c299f3f91429abf2d8013fc0f56fb
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728878

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