Triethylamine → Ethyl 3-ethoxy-3-imino-2-(cyclopropyloxyimino)propionate

HRID 1723582Notes

Reaction equation

HRID 1723582 reaction equation
[C:1]([C:4](=[N:10][O:11][CH:12]1[CH2:14][CH2:13]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[NH2:2].F[B-](F)(F)F.[CH2:20]([O+](CC)CC)[CH3:21].C(N(CC)CC)C>C(Cl)Cl.C(OC(C)C)(C)C>[CH2:20]([O:3][C:1](=[NH:2])[C:4](=[N:10][O:11][CH:12]1[CH2:13][CH2:14]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2723982Triethyloxonium tetrafluoroborateHCID 54332569Ethyl 2-carbamoyl-2-(cyclopropyloxyimino)acetate

Product 1

HCID 54045971Ethyl 3-ethoxy-3-imino-2-(cyclopropyloxyimino)propionate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A mixture of ethyl 2-carbamoyl-2-(cyclopropyloxyimino)acetate (syn isomer)(8.14 g) and triethyloxonium fluoroborate (11.5 g) in methylene chloride (110 ml) was stirred at ambient temperature for 16 hours. To the mixture was added triethylamine (17 ml) under ice-cooling. The mixture was washed with water, dried over sodium sulfate, and concentrated in vacuo to give a residue. The residue was dissolved in diisopropyl ether. The solution was washed with water, dried over sodium sulfate, and concentrated in vacuo to give ethyl 3-ethoxy-3-imino-2-(cyclopropyloxyimino)propionate (syn isomer(9.60 g) as an oil.

Workup

  1. temperaturecooling
  2. washThe mixture was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a residue
  6. washThe solution was washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a000c672e084d6b85217dddf91b9d0e
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

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