2,5-Hexanedione → HCID 21877666, compound

HRID 1991268Notes

Reaction equation

HRID 1991268 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH2:5].[CH2:10]([CH2:14][C:15](=O)[CH3:16])[C:11]([CH3:13])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[C:15]([CH3:16])=[CH:14][CH:10]=[C:11]2[CH3:13])[CH:6]=[C:7]([F:9])[CH:8]=1

Participants

5

Reactant 3

HCID 80352,5-HexanedioneHCID 965953,5-DifluoroanilineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 21877666HCID 21877666, compound

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

To the solution of 3,5-difluoroaniline (3.53 g, 26.8 mmol) in toluene/THF (1:1, 60 mL) is added acetonylacetone (3.24 mL, 26.8 mmol) and p-toluenesulfonic acid monohydrate (0.168 g). The reaction mixture is heated at reflux for 3 h, concentrated under reduced pressure, diluted with CH2Cl2 (60 mL), washed with water (3×10 mL) and saline (2×20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by chromatography on a Biotage Flash 40M 90 g silica gel cartridge eluting with EtOAc/Hexanes (5/95-10/90) affords the title compound, mp 55-56° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with CH2Cl2 (60 mL)
  5. washwashed with water (3×10 mL) and saline (2×20 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customPurification by chromatography on a Biotage Flash 40M 90 g silica gel cartridge
  9. washeluting with EtOAc/Hexanes (5/95-10/90)

Sources & evidence

ORD record
ord-186204d5f24447b8919beb30efb70d3a
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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