Tetrahydrofuran → HCID 18071782, compound

HRID 1526325Notes

Reaction equation

HRID 1526325 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[O:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.C([O-])(=[O:17])C.[Na+]>O>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH:4][C:11](=[O:10])[CH2:12][C:13](=[O:17])[CH3:14]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 796472,6-DifluoroanilineHCID 517045Sodium Acetate

Product 1

HCID 18071782HCID 18071782, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2,6-difluoroaniline (5.00 g), 2,2,6-trimethyl-4H-1,3-didioxin-4-one (7.16 g) and tetrahydrofuran (13 mL) was added sodium acetate (3.18 g) at room temperature. The reaction mixture was refluxed overnight, and cooled to room temperature. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (5.04 g).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6cbc82bc747f41d29cb55f6b063ab690
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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