1,1,1-Trifluoro-2,4-pentanedione → HCID 178437489, compound

HRID 885418Notes

Reaction equation

HRID 885418 reaction equation
Cl.[C:2](=[NH:8])(OCC)[CH2:3][CH3:4].Cl.[NH2:10][CH2:11][C:12]#[N:13].[F:14][C:15]([F:23])([F:22])[C:16](=O)[CH2:17][C:18](=O)[CH3:19].C(N(C(C)C)CC)(C)C>ClCCCl.C(OCC)(=O)C>[CH2:3]([C:2]1[NH:8][C:11]2=[N:10][C:18]([CH3:19])=[CH:17][C:16]([C:15]([F:23])([F:22])[F:14])=[C:12]2[N:13]=1)[CH3:4]

Participants

7

Reactant 4

HCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 81531DiisopropylethylamineHCID 11491918Aminoacetonitrile hydrochlorideHCID 13000588Ethyl propanecarboximidate hydrochloride

Product 1

HCID 178437489HCID 178437489, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl propionimidate hydrochloride (1.37 g, 10.0 mmol), aminoacetonitrile hydrochloride (0.93 g, 10.0 mmol), 1,1,1-trifluoro-2,4-pentanedione (3.64 mL, 30.0 mmol) and diisopropylethylamine (5.23 mL, 30.0 mmol) were stirred in 1,2-dichloroethane (50 mL) under reflux for 4 hr. Ethyl acetate was added to the mixture, and the mixture was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/70) to give the title compound (1.07 g, 47%).

Workup

  1. temperatureunder reflux for 4 hr
  2. washthe mixture was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/70)

Sources & evidence

ORD record
ord-82b8906f29294553abd2ddc13c046729
Source dataset
uspto-grants-2012_08
Patent number
US08242151B2

Reaction notes

Loading…