Sodium Chloride → Ethyl 2-amino-2-cyanoacetate

HRID 73601

Reaction equation

HRID 73601 reaction equation
[C:1]([C:3](=[N:9]O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[O-]S(S([O-])=O)=O.[Na+].[Na+].[Cl-].[Na+]>O.C(=O)(O)[O-].[Na+]>[NH2:9][CH:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 24489Sodium DithioniteHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 288716Ethyl 2-amino-2-cyanoacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of ethyl 2-cyano-2-(hydroxyimino)acetate (1 eq) in 70 mL of water and 56 mL of aq. sat. sodium bicarbonate was added portionwise throughout 10 minutes Na2S2O4 (2.8 eq) The reaction mixture was stirred at room temperature for 1 hour. The solution was saturated with sodium chloride, extracted with methylene chloride (300 mL×3) and then the combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give the titled compound, which was used to next step without further (55%). LC/MS (m/z): 129.0 (MH+), Rt:0.25 min.

Workup

  1. extractionextracted with methylene chloride (300 mL×3)
  2. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-104f0b7a1d864791bee83ff07934004f
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Linked notes

Loading…