Acetonitrile, 2,2-diethoxy- → Methyl 2,2-diethoxyethanecarboximidate

HRID 2036836Notes

Reaction equation

HRID 2036836 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[N:6])[CH3:2].[CH3:10][O-:11].[Na+]>CO>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5](=[NH:6])[O:11][CH3:10])[CH3:2]

Participants

4

Reactant 2

HCID 80223Acetonitrile, 2,2-diethoxy-HCID 10942334Sodium Methoxide

Product 1

HCID 17874536Methyl 2,2-diethoxyethanecarboximidateYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of diethoxyacetonitrile (5 g, 38.75 mmol) in dry methanol (80 mL) was added 1 mL of a 20% solution of sodium methoxide. After the addition, the reaction mixture was stirred at RT for 24 h, quenched with solid CO2, and then concentrated. The resulting residue was diluted with water and extracted with chloroform. The organic layer was washed with brine and dried over Na2SO4 to yield methyl 2,2-diethoxyacetimidate (6 g, 96%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.95 (s, 1H),), 4.82 (s, 1H), 3.66 (s, 3H), 3.49 (q, 4H, J=7.2 Hz); 1.16-1.13 (t, 3H, J=7.2 Hz).

Workup

  1. additionAfter the addition
  2. customquenched with solid CO2
  3. concentrationconcentrated
  4. additionThe resulting residue was diluted with water
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-511b59abb7fb479f996b4c64f01fc80a
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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