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

HRID 718151Notes

Reaction equation

HRID 718151 reaction equation
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]

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d91bb8436c7344b29e088efac8c90f08
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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