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

HRID 718151ノート

反応式

HRID 718151 の反応式
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]

参加物

4

反応物 3

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

生成物 1

HCID 53746597Ethyl N-(ethoxycarbonyl)-2-methylpropanimidate収率 99%

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d91bb8436c7344b29e088efac8c90f08
出典データセット
uspto-grants-2015_11
特許番号
US09193719B2

反応ノート

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