Tetrahydrofuran → HCID 59443012, compound

HRID 1959114Notes

Reaction equation

HRID 1959114 reaction equation
[CH3:1][C:2](=O)[CH2:3][CH2:4][C:5](=O)[CH3:6].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[C:27]([F:29])[CH:28]=1)[NH2:25].O1CCCC1>C1(C)C=CC=CC=1>[Cl:21][C:22]1[CH:23]=[C:24]([N:25]2[C:5]([CH3:6])=[CH:4][CH:3]=[C:2]2[CH3:1])[CH:26]=[C:27]([F:29])[CH:28]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 80352,5-HexanedioneHCID 521998p-Toluenesulfonic acid monohydrateHCID 27348383-Chloro-5-fluoroaniline

Product 1

HCID 59443012HCID 59443012, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,5-Hexanedione (4.51 mL) and p-toluenesulfonic acid monohydrate (73 mg) were added to a solution of 3-chloro-5-fluoroaniline (5.12 g) in toluene (40 mL)-tetrahydrofuran (40 mL), and the mixture was heated under reflux for 3.5 hours. After being cooled down, the reaction solution was concentrated in vacuo, and the resultant residue was dissolved in chloroform. The solution was washed successively with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulted residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=97/3) to give the titled compound (7.63 g) as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3.5 hours
  3. temperatureAfter being cooled down
  4. concentrationthe reaction solution was concentrated in vacuo
  5. dissolutionthe resultant residue was dissolved in chloroform
  6. washThe solution was washed successively with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe resulted residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=97/3)

Sources & evidence

ORD record
ord-c6660619707844e7b297b10fe46f05c5
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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