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

HRID 1074340Notes

Reaction equation

HRID 1074340 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)propionateYield 69.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A mixture of ethyl 2-carbamoyl-2-(cyclopropyloxyimino)acetate (syn isomer)(84.1 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-9b55814a15714c82b1b99405d98beb96
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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