Ethyl 2-amino-2-cyanoacetate → Ethyl 2-cyano-2-formamidoacetate

HRID 1170899

Reaction equation

HRID 1170899 reaction equation
[NH2:1][CH:2]([C:8]#[N:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:10](OCC#N)=[O:11]>ClCCl>[C:8]([CH:2]([NH:1][CH:10]=[O:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4])#[N:9]

Participants

4

Reactant 2

HCID 288716Ethyl 2-amino-2-cyanoacetateHCID 4205685(Formyloxy)acetonitrile

Product 1

HCID 12562418Ethyl 2-cyano-2-formamidoacetateYield 51.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To ethyl 2-amino-2-cyanoacetate (800 mg, 6.24 mmol) in dichloromethane (5 mL) was added cyanomethyl formate (531 mg, 6.24 mmol) in dichloromethane (5 mL) dropwise at 0° C. The reaction was warmed up to room temperature for twelve hours. The reaction was concentrated and purified by silica gel chromatography to give an oil of ethyl 2-cyano-2-formamidoacetate (500 mg). NMR spectrum shows a mixture of starting material and desired product in a 1:1 ratio. The product was dissolved in methylene chloride (10 mL). To this solution was added cyanomethyl formate (797 mg, 9.37 mmol) and the reaction was stirred for twelve more hours. The reaction was concentrated and purified with silica gel chromatography to give an oil of ethyl 2-cyano-2-formamidoacetate (460 mg). 1H NMR (400 MHz, CDCl3) δ 8.30 (s, 1H), 6.61 (s, 1H), 5.55 (d, 2H), 4.36 (q, 2H), 1.35 (t, 3H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-5731a8085595424fa69acfa77427fea3
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Linked notes

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