Hydrochloric Acid → HCID 10750851, compound

HRID 1976064Notes

Reaction equation

HRID 1976064 reaction equation
[Na].[N+:2]([CH2:5][C:6]([NH2:8])=[O:7])([O-:4])=[O:3].[F:9][C:10]([C:13]([CH:15]=[CH:16]OCC)=O)([F:12])[F:11].Cl>C(O)C>[N+:2]([C:5]1[C:6](=[O:7])[NH:8][C:13]([C:10]([F:12])([F:11])[F:9])=[CH:15][CH:16]=1)([O-:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2792562-NitroacetamideHCID 27803954-Ethoxy-1,1,1-trifluoro-3-buten-2-oneHCID 5360545Sodium

Product 1

HCID 10750851HCID 10750851, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethanol (1 L) was slowly added sodium metal (4.83 g, 0.21 mol). Once the metal had dissolved, nitroacetamide (21.8 g, 0.21 mol) and (2-ethyloxyvinyl) trifluoromethyl ketone (35 g, 0.21 mol) were added, and the suspension formed was heated at reflux for 16 hrs. The resulting mixture was acidified with aqueous hydrochloric acid (1 M) and concentrated in vacuo. The residue was taken up in ethyl acetate (1 L) and the solid formed removed by filtration. The filtrate was then concentrated and the residue purified by silica chromatography to give the product as an orange solid (25.9 g, 0.12 mol, 59% yield).

Workup

  1. dissolutionOnce the metal had dissolved
  2. customthe suspension formed
  3. temperaturewas heated
  4. temperatureat reflux for 16 hrs
  5. concentrationconcentrated in vacuo
  6. customthe solid formed
  7. customremoved by filtration
  8. concentrationThe filtrate was then concentrated
  9. customthe residue purified by silica chromatography

Sources & evidence

ORD record
ord-6e05d26049324feea4852c41cef80c9f
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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