Ethyl trifluoroacetate → HCID 178517786, compound

HRID 351400Notes

Reaction equation

HRID 351400 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[F:12][C:13]([F:20])([F:19])[C:14](OCC)=O.[O-]CC.[Na+].CC(O)=O.O>C(O)C>[Cl:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[C:14]([C:13]([F:20])([F:19])[F:12])[N:6]=[C:4]2[OH:5]

Participants

6

Reactant 4

HCID 9794Ethyl trifluoroacetateHCID 788762-Amino-5-chlorobenzamideHCID 2723922Sodium ethoxideHCID 21899381Acetic acid--water (1/1)

Product 1

HCID 178517786HCID 178517786, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Amino-5-chlorobenzamide (Avocado)(1.00 g, 5.86 mmol, 1.0 eq.) and ethyl trifluoroacetate (4.19 mL, 35.2 mmol, 6.0 eq.) were dissolved in 50 mL of ethanol at rt under nitrogen and followed by the addition of 3.09 M sodium ethoxide in ethanol (11.38 mL, 35.2 mmol, 6.0 eq.) The mixture was refluxed 20 hours. Cooled to rt. Added 10 mL of 10% HOAc/H2O. Solids formed which were filtered, rinsed with 5 mL H2O, then dissolved in 20 mL of EtOAc/THF. Dried and stripped in vacuo to give 1.35 g of amber solids. LCMS detects (M+H)+=249.

Workup

  1. temperaturewas refluxed 20 hours
  2. customSolids formed which
  3. filtrationwere filtered
  4. washrinsed with 5 mL H2O
  5. dissolutiondissolved in 20 mL of EtOAc/THF
  6. customDried

Sources & evidence

ORD record
ord-aca0adabeade49c2af4bc0682854cb96
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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