Cyanoacetamide → HCID 13702657, compound

HRID 1794599Notes

Reaction equation

HRID 1794599 reaction equation
[F:1][C:2]([F:8])([F:7])[C:3](Br)=[N:4][OH:5].[C:9]([CH2:11][C:12]([NH2:14])=[O:13])#[N:10].[O-]CC.[Na+]>CCO>[NH2:10][C:9]1[O:5][N:4]=[C:3]([C:2]([F:8])([F:7])[F:1])[C:11]=1[C:12]([NH2:14])=[O:13]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 2723922Sodium ethoxideHCID 713630332,2,2-Trifluoro-N-hydroxyethanimidoyl bromide

Product 1

HCID 13702657HCID 13702657, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of trifluoroacetohydroximoyl bromide etherate (17.6 g, 91.6 mmol) in 20 mL of EtOH was added to a solution of 2-cyano-acetamide (7.7 g, 91.6 mmol) and sodium ethoxide (6.2 g, 91.6 mmol) in ethanol (300 mL). After stirring at room temperature for 3 h, the solvent was removed. The residue was diluted with EtOAc and washed with water, brine, and dried over MgSO4. The organic phase was filtered and concentrated to give a brown oil. The product was purified by a flash chromatography on SiO2 eluting with hexanes:EtOAc (3:1) to give 7 as a light yellow solid (11 g, 40%); MS (ESI): 196 (M+H)+. Ref: J. Heterocyclic Chem. 1535 (1986).

Workup

  1. customthe solvent was removed
  2. additionThe residue was diluted with EtOAc
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationThe organic phase was filtered
  6. concentrationconcentrated
  7. customto give a brown oil
  8. customThe product was purified by a flash chromatography on SiO2 eluting with hexanes:EtOAc (3:1)

Sources & evidence

ORD record
ord-0284a071b8c04016b36038446b755bc2
Source dataset
uspto-grants-2006_04
Patent number
US07022850B2

Reaction notes

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