Trifluoroacetamidine → HCID 136088685, compound

HRID 1742021Notes

Reaction equation

HRID 1742021 reaction equation
C([C:3]([C:10](=O)[CH3:11])([CH2:7][CH2:8][CH3:9])[C:4]([OH:6])=O)C.[Na].[F:14][C:15]([F:20])([F:19])[C:16]([NH2:18])=[NH:17]>CCO>[CH3:11][C:10]1[N:17]=[C:16]([C:15]([F:20])([F:19])[F:14])[NH:18][C:4](=[O:6])[C:3]=1[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 2776882TrifluoroacetamidineHCID 5360545SodiumHCID 19009737HCID 19009737, compound

Product 1

HCID 136088685HCID 136088685, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-acetylpentanoic acid (17.2 g, 0.1 mol) in absolute EtOH was treated with 2.3 g, 0.1 mol) sodium until the metal was dissolved. Trifluoroacetamidine (11.5 g, 0.1 mol) was added and the mixture was refluxed for 3 h, then evaporated to dryness. The residue was taken up in H2O, acidified with 2N HCl, and extracted with EtOAc. The organic layer was washed with water (twice), dried, and evaporated to give an oil. Purification by flash chromatography (CH2Cl2, CH2Cl2 -EtOAc 5%) afforded 7.5 g (34%) of the desired compound as crystals.

Workup

  1. dissolutionwas dissolved
  2. temperaturethe mixture was refluxed for 3 h
  3. customevaporated to dryness
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with water (twice),
  6. customdried
  7. customevaporated
  8. customto give an oil
  9. customPurification by flash chromatography (CH2Cl2, CH2Cl2 -EtOAc 5%)

Sources & evidence

ORD record
ord-9abb9c0497bc4ee28f618c5b2b918611
Source dataset
uspto-grants-1994_08
Patent number
US05336677

Reaction notes

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