2,4,6-Trimethylpyridine → Ethyl N-(ethoxycarbonyl)-2-methylpropanimidate

HRID 718151노트

반응식

HRID 718151 반응식
Cl.[C:2](=[NH:9])([O:6][CH2:7][CH3:8])[CH:3]([CH3:5])[CH3:4].N1C(C)=CC(C)=CC=1C.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>>[CH2:23]([O:22][C:20]([N:9]=[C:2]([O:6][CH2:7][CH3:8])[CH:3]([CH3:5])[CH3:4])=[O:21])[CH3:24]

참가 물질

4

반응물 3

HCID 79532,4,6-TrimethylpyridineHCID 10928Ethyl chloroformateHCID 12816252Ethyl 2-methylpropanimidate--hydrogen chloride (1/1)

생성물 1

HCID 53746597Ethyl N-(ethoxycarbonyl)-2-methylpropanimidate수율 99%

반응 조건

온도
0 °C

실험 절차

Ethyl isobutyrimidate hydrochloride (1.8 g, 11.9 mmol) was suspended in hexanes (29.7 mL) and cooled to 0° C. 2,4,6-Collidine (4.1 mL, 30.9 mmol) and ethyl chloroformate (1.9 g, 17.8 mmol) were sequentially added and the mixture was allowed to warm to RT and stirred for 12 h. Organic solvent was removed in vacuo. The residue was suspended in EtOAc (50 mL) and solids were removed by filtration through a pad of diatomaceous earth. The filter cake was washed with EtOAc (3×10 mL) and the combined filtrates were concentrated in vacuo to afford ethyl N-ethoxycarbonylisobutyrimidate (2.2 g, 99%) as a yellow amorphous solid. 1H NMR (400 MHz, DMSO-d6): δ 4.09 (q, J=7.1 Hz, 2H), 4.03 (q, J=7.1 Hz, 2H), 2.65-2.64 (m, 1H), 1.20 (t, J=7.1 Hz, 3H), 1.19 (t, J=7.1 Hz, 3H), 1.07 (d, J=6.8 Hz, 6H).

후처리

  1. temperatureto warm to RT
  2. customOrganic solvent was removed in vacuo
  3. customsolids were removed by filtration through a pad of diatomaceous earth
  4. washThe filter cake was washed with EtOAc (3×10 mL)
  5. concentrationthe combined filtrates were concentrated in vacuo

출처 및 근거

ORD 기록
ord-d91bb8436c7344b29e088efac8c90f08
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193719B2

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