Pyridine → ethyl N-ethoxycarbonyl-2-methoxyacetimidate

HRID 718157Notes

Reaction equation

HRID 718157 reaction equation
Cl.[CH3:2][O:3][CH2:4][C:5](=[NH:9])[O:6][CH2:7][CH3:8].N1C=CC=CC=1.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18].CCOC(C)=O>C(Cl)Cl>[CH2:20]([O:19][C:17]([N:9]=[C:5]([O:6][CH2:7][CH3:8])[CH2:4][O:3][CH3:2])=[O:18])[CH3:21]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 12816254Ethyl 2-methoxyethanecarboximidate hydrochloride

Product 1

HCID 90426579ethyl N-ethoxycarbonyl-2-methoxyacetimidateYield 102.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-methoxyacetimidate hydrochloride (0.95 g, 6.18 mmol) was suspended in DCM (12.4 mL) and the mixture was cooled to 0° C. Pyridine (2.5 mL, 30.9 mmol) and ethyl chloroformate (1.2 mL, 12.4 mmol) were added sequentially and the solution was allowed to warm to RT and stirred for 12 h. EtOAc (100 mL) was added and solids were removed by filtration through a pad of diatomaceous earth. The filtrate was concentrated in vacuo to afford ethyl N-ethoxycarbonyl-2-methoxyacetimidate (1.2 g, 100%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 4.08-4.03 (m, 2H), 3.90 (q, J=7.0 Hz, 4H), 3.20 (s, 3H), 1.11 (t, J=6.9 Hz, 6H).

Workup

  1. temperatureto warm to RT
  2. customsolids were removed by filtration through a pad of diatomaceous earth
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-016e56860629486287be1f3e1f7ef90b
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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