Acetic Acid → Methyl 3-imino-3-methoxy-2-ethoxyiminopropionate

HRID 647111Notes

Reaction equation

HRID 647111 reaction equation
[C:1]([C:3](=[N:8][O:9][CH2:10][CH3:11])[C:4]([O:6][CH3:7])=[O:5])#[N:2].C[O-].[Na+].C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)O[C:21](=[O:22])C=2C=1.C(O)(=O)C>CO>[NH:2]=[C:1]([O:22][CH3:21])[C:3](=[N:8][O:9][CH2:10][CH3:11])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4764PhenolphthaleinHCID 10942334Sodium MethoxideHCID 53675257Methyl 2-cyano-2-ethoxyiminoacetate

Product 1

HCID 54122709Methyl 3-imino-3-methoxy-2-ethoxyiminopropionate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-cyano-2-ethoxyiminoacetate (syn isomer) (4.7 g) in methanol (50 ml) was added 1 N methanolic solution (5 ml) of sodium methoxide under cooling in an ice-bath and stirring, which was continued for 20 minutes in an ice-bath and 15 minutes at room temperature. The mixture was neutralized to the end point of phenolphthalein with 1 N methanolic solution of acetic acid and evaporated. The residue was dissolved in methylene chloride (80 ml), washed with water, dried over magnesium sulfate and evaporated to give methyl 3-imino-3-methoxy-2-ethoxyiminopropionate (syn isomer) (4.8 g) as an oil.

Workup

  1. temperatureunder cooling in an ice-bath
  2. customevaporated
  3. dissolutionThe residue was dissolved in methylene chloride (80 ml)
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-d0490670f8fa4ae5adf7b8a6a6770d0a
Source dataset
uspto-grants-1983_10
Patent number
US04407798

Reaction notes

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