Chlorosuccinimide → HCID 86611470, compound

HRID 910374Notes

Reaction equation

HRID 910374 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:30]([F:33])([F:32])[F:31])[O:13][N:12]=[C:11]([C:14]3[CH:27]=[CH:26][C:17]([C:18]([NH:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[O:19])=[C:16]([S:28][CH3:29])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClN1C(=[O:40])CCC1=O>ClCCCl.O>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2([C:30]([F:33])([F:32])[F:31])[O:13][N:12]=[C:11]([C:14]3[CH:27]=[CH:26][C:17]([C:18]([NH:20][CH2:21][C:22]([F:23])([F:25])[F:24])=[O:19])=[C:16]([S:28]([CH3:29])=[O:40])[CH:15]=3)[CH2:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 86611471HCID 86611471, compound

Product 1

HCID 86611470HCID 86611470, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

In a solution of 0.38 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylthio-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-322) synthesized similarly to Synthetic Example 13 in 6 ml of 1,2-dichloroethane, 0.10 g of N-chlorosuccinic acid imide was added with stirring at room temperature, and stirred at the same temperature for 11 hours. After the completion of the reaction, the reaction mixture was poured in 30 ml of water, and extracted with ethyl acetate (20 ml×3). The organic phase was washed with 30 ml of saturated sodium hydrogen carbonate, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2), and 0.17 g of the aimed product was obtained as colorless oily substance.

Workup

  1. stirringstirred at the same temperature for 11 hours
  2. customAfter the completion of the reaction
  3. extractionextracted with ethyl acetate (20 ml×3)
  4. washThe organic phase was washed with 30 ml of saturated sodium hydrogen carbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-b72ac0f633eb4c4090cf6e51d21435db
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

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