Formic Acid → Ethyl 2-cyano-2-formamidoacetate

HRID 521819Notes

Reaction equation

HRID 521819 reaction equation
N#N.[CH:3](O)=[O:4].CC(OC(C)=O)=O.[NH2:13][CH:14]([C:20]#[N:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C1COCC1>[C:20]([CH:14]([NH:13][CH:3]=[O:4])[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:21]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 947NitrogenHCID 7918Acetic AnhydrideHCID 288716Ethyl 2-amino-2-cyanoacetate

Product 1

HCID 12562418Ethyl 2-cyano-2-formamidoacetateYield 70.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere (N2), HCOOH (2.44 g, 53 mmol) was added to Ac2O (6.48 g, 63.6 mmol) at 0° C. After it was allowed to warm to ambient temperature the reaction was heated at 50° C. for 15 hr. It was allowed to cool to ambient temperature. This mixed acid anhydride was then added dropwise to a solution of ethyl 2-amino-2-cyanoacetate (128 mg, 1 mmol) in dry THF (5 mL) at 0° C. After the cooling bath was removed, the reaction was maintained at ambient temperature for additional 1 hr. The reaction mixture was concentrated and purified by silica gel column chromatography (5:1 PE/EtOAc) to afford ethyl 2-cyano-2-formamidoacetate (110 mg, 70%) as a white solid.

Workup

  1. temperaturewas heated at 50° C. for 15 hr
  2. temperatureto cool to ambient temperature
  3. customAfter the cooling bath was removed
  4. temperaturethe reaction was maintained at ambient temperature for additional 1 hr
  5. concentrationThe reaction mixture was concentrated
  6. custompurified by silica gel column chromatography (5:1 PE/EtOAc)

Sources & evidence

ORD record
ord-252f0a4a027345c8854b0dda4dda9d7d
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

Loading…