Ethyl formate → Sodium (E)-2-cyano-2-[(methoxycarbonyl)(methyl)amino]ethenolate

HRID 346532Notes

Reaction equation

HRID 346532 reaction equation
C[O-].[Na+:3].[C:4]([CH2:6][N:7]([CH3:12])[C:8](=[O:11])[O:9][CH3:10])#[N:5].[CH:13](OCC)=[O:14]>O1CCCC1>[C:4](/[C:6](/[N:7]([C:8]([O:9][CH3:10])=[O:11])[CH3:12])=[CH:13]\[O-:14])#[N:5].[Na+:3]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 10942334Sodium MethoxideHCID 45087346Methyl cyanomethyl(methyl)carbamate

Product 1

HCID 57469797Sodium (E)-2-cyano-2-[(methoxycarbonyl)(methyl)amino]ethenolate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

0.46 g (0.01 mmol) of sodium methoxide is added under argon to tetrahydrofuran (solution A). Then 1.00 g (0.01 mmol) of methyl cyanomethyl(methyl)carbamate from Example 9A is added to 1.73 g (0.02 mmol) of ethyl formate. Solution A is slowly added dropwise to this mixture. The mixture is stirred at RT overnight. The solvent is concentrated in vacuo in a rotary evaporator, and diethyl ether is added to the residue. The crystals which have separated out are filtered off with suction and dried under high vacuum.

Workup

  1. concentrationThe solvent is concentrated in vacuo in a rotary evaporator, and diethyl ether
  2. additionis added to the residue
  3. customThe crystals which have separated out
  4. filtrationare filtered off with suction
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-78a196e817e64eb8ab1ec95dfae2af59
Source dataset
uspto-grants-2007_02
Patent number
US07173037B2

Reaction notes

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