Chlorosuccinimide → HCID 71615482, compound

HRID 885808Notes

Reaction equation

HRID 885808 reaction equation
[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[CH:7]=[N:8][OH:9].ClN1C(=O)CCC1=O.[Cl:20][C:21]1[CH:22]=[C:23]([C:28]([C:30]([F:33])([F:32])[F:31])=[CH2:29])[CH:24]=[C:25]([Cl:27])[CH:26]=1.C(=O)([O-])O.[K+]>COCCOC.C(OCC)(=O)C.O>[Cl:20][C:21]1[CH:22]=[C:23]([C:28]2([C:30]([F:33])([F:31])[F:32])[O:9][N:8]=[C:7]([C:6]3[CH:5]=[N:4][C:3]([Cl:11])=[C:2]([Cl:1])[CH:10]=3)[CH2:29]2)[CH:24]=[C:25]([Cl:27])[CH:26]=1

Participants

8

Reactant 4

HCID 31398ChlorosuccinimideHCID 516893Potassium BicarbonateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 72643026HCID 72643026, compound

Product 1

HCID 71615482HCID 71615482, compoundYield 38.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

In a solution of 2.1 g of 5,6-dichloronicotine aldehyde oxime in 30 mL of 1,2-dimethoxyethane, 2.3 g of N-chlorosuccinimide was added, and stirred at 70° C. for 4 hours. Then, the reaction mixture was left and cooled to room temperature, 2.5 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 1, 1.4 g of potassium hydrogen carbonate and 2.0 mL of water were added and continued to stir at room temperature further for 20 hours. After the completion of the reaction, the reaction mixture was diluted with 70 mL of ethyl acetate, washed with water (50 mL×1), and the organic was dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled off under reduced pressure. The residue was purified with medium pressure preparative liquid chromatography (medium pressure collection apparatus: YFLC-Wprep manufactured by Yamazen Corporation) that was eluted with ethyl acetate-hexane (gradient of 1:10 to 1:5) to obtain 1.7 g of the aimed products as white crystal.

Workup

  1. waitThen, the reaction mixture was left
  2. temperaturecooled to room temperature
  3. stirringto stir at room temperature further for 20 hours
  4. customAfter the completion of the reaction
  5. washwashed with water (50 mL×1)
  6. dry with materialdried over saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified with medium pressure preparative liquid chromatography (medium pressure collection apparatus: YFLC-Wprep manufactured by Yamazen Corporation) that
  9. washwas eluted with ethyl acetate-hexane (gradient of 1:10 to 1:5)

Sources & evidence

ORD record
ord-51cac5f3eb1d4ab7852400e6a778d680
Source dataset
uspto-grants-2012_08
Patent number
US08242283B2

Reaction notes

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