Azobisisobutyronitrile → HCID 86631566, compound

HRID 551331Notes

Reaction equation

HRID 551331 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Br:24])[C:21]([F:25])=[C:20]([Br:26])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].BrN1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[C:47]1(=[O:57])[NH:51][C:50](=[O:52])[C:49]2=[CH:53][CH:54]=[CH:55][CH:56]=[C:48]12.[K]>ClCCCl.CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Br:24])[C:21]([F:25])=[C:20]([Br:26])[CH:19]=3)([C:14]([F:17])([F:15])[F:16])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][N:51]1[C:50](=[O:52])[C:49]2=[CH:53][CH:54]=[CH:55][CH:56]=[C:48]2[C:47]1=[O:57]

Participants

8

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 24194345Phthalimide potassium saltHCID 86631567HCID 86631567, compound

Product 1

HCID 86631566HCID 86631566, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(3-chloro-4-methylphenyl)-5-(3,5-dibromo-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole (1.1 g) in 1,2-dichloroethane (7 mL) was added N-bromosuccinimide (0.38 g) and 2,2′-azobis(2-methylpropionitrile) (0.028 g). The mixture was heated to reflux for 3 hours and then cooled to room temperature. The resulting mixture was diluted with 1,2-dichloroethane (10 mL), washed with water (30 mL) and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide a residue. The residue was dissolved in N,N-dimethylformamide (7 mL), and potassium phthalimide (0.40 g) was added. The mixture was stirred at room temperature for 15 hours. The reaction mixture was then poured into water (10 mL) and extracted with ethyl acetate (10 mL×2). The organic extracts were combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the crude title compound as a pale yellow resin (0.75 g), which was used in the next step without purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. washwashed with water (30 mL) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide a residue
  7. extractionextracted with ethyl acetate (10 mL×2)
  8. washwashed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f2afdbc1edd4589a2aa39c50beb8b9b
Source dataset
uspto-grants-2011_05
Patent number
US07947715B2

Reaction notes

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