Pyridine → HCID 90427775, compound

HRID 718155Notes

Reaction equation

HRID 718155 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH2:5][C:6](=[NH:10])[O:7][CH2:8][CH3:9].N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(Cl)Cl.CCOC(C)=O>[CH2:21]([O:20][C:18]([N:10]=[C:6]([O:7][CH2:8][CH3:9])[CH2:5][CH2:4][O:3][CH3:2])=[O:19])[CH3:22]

Participants

6

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 86200540HCID 86200540, compound

Product 1

HCID 90427775HCID 90427775, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 3-methoxypropanimidate hydrochloride (1.0 g, 6.0 mmol) was suspended in DCM (12 mL) and cooled to 0° C. Pyridine (2 mL, 24.7 mmol) was added dropwise and the mixture was stirred for 15 min. Ethyl chloroformate (0.97 g, 9.0 mmol) was added dropwise and the mixture was diluted with DCM (20 mL), allowed to warm to RT, and stirred for 12 h. The mixture was diluted with a mixture of EtOAc and hexanes (1:1, 200 mL) and the solids were removed by filtration through a pad of diatomaceous earth. The filtrate was concentrated in vacuo to afford ethyl N-ethoxycarbonyl-3-methoxy-propanimidate (1.0 g, 83%) as a light green solid. 1H NMR (400 MHz, DMSO-d6): δ 4.08 (q, J=7.0 Hz, 2H), 4.05 (q, J=7.0 Hz, 2H), 3.50 (t, J=6.4 Hz, 2H), 3.19 (s, 3H), 2.57 (t, J=6.4 Hz, 2H), 1.20 (t, J=7.0 Hz, 3H), 1.19 (t, J=7.0 Hz, 3H).

Workup

  1. temperatureto warm to RT
  2. stirringstirred for 12 h
  3. customthe solids were removed by filtration through a pad of diatomaceous earth
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-096f776bad7040a38421832bf2326ee7
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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