Formic Acid → Ethyl 2-cyano-2-formamidoacetate

HRID 1185252Notes

Reaction equation

HRID 1185252 reaction equation
[CH:1](O)=[O:2].CC(OC(C)=O)=O.[NH2:11][CH:12]([C:18]#[N:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1COCC1>[C:18]([CH:12]([NH:11][CH:1]=[O:2])[C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:19]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 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 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-06f96c78d0e84ff9814b6647a887a215
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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