Carbon Dioxide → Methyl 2,2-diethoxyethanecarboximidate

HRID 1767746Notes

Reaction equation

HRID 1767746 reaction equation
C[O-].[Na+].[CH2:4]([O:6][CH:7]([O:10][CH2:11][CH3:12])[C:8]#[N:9])[CH3:5].[C:13](=O)=[O:14]>CO>[CH2:4]([O:6][CH:7]([O:10][CH2:11][CH3:12])[C:8](=[NH:9])[O:14][CH3:13])[CH3:5]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 80223Acetonitrile, 2,2-diethoxy-HCID 10942334Sodium Methoxide

Product 1

HCID 17874536Methyl 2,2-diethoxyethanecarboximidateYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of sodium methoxide (3.54 ml of a 25% wt. solution in methanol, 15.5 mmol) in methanol (80 ml) was added diethoxyacetonitrile (215 ml, 155 mmol) and the reaction mixture stirred for 4 hours at room temperature. Solid carbon dioxide was added and most of the methanol was removed in vacuo. Diethyl ether (30 ml) was added and the sodium carbonate removed by filtration. The residue was concentrated to afford methyl diethoxyacetimidate as a colourless oil (22 g, 92% yield) which was used with no further purification.

Workup

  1. customwas removed in vacuo
  2. additionDiethyl ether (30 ml) was added
  3. customthe sodium carbonate removed by filtration
  4. concentrationThe residue was concentrated

Sources & evidence

ORD record
ord-d74c79b8ef7045b5bc30488b1dab9d64
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

Loading…