HCID 67165066, compound → HCID 135927331, compound

HRID 878832Notes

Reaction equation

HRID 878832 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:28])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[C:16]([CH2:23][CH3:24])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1>COC(OC)N(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:26])([F:28])[F:27])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:20]/[CH:11]=[N:12]\[O:13][CH3:9])=[O:19])=[C:16]([CH2:23][CH3:24])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

3

Reactant 1

HCID 67165066HCID 67165066, compound

Product 1

HCID 135927331HCID 135927331, compoundYield 147.2%

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A mixture of 0.18 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-ethyl benzoic acid amide and 10 mL of N,N-dimethylformamide dimethylacetal was stirred under reflux with heating for 4 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 5 mL of 1,4-dioxane, and added dropwise in a solution of 0.10 g of methoxyamine hydrochloride and 0.10 g of sodium hydroxide in 4 mL of water and 4 mL of acetic acid. After the completion of the addition dropwise, it was continued to stir at room temperature further for 30 minutes. After the completion of the reaction, 10 mL of water was added in the reaction mixture, and extracted with ethyl acetate (40 mL×1). The organic phase was dehydrated with and dried over saturated sodium chloride and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (2:3) to obtain 0.15 g of the aimed product as colorless resinous substance.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 4 hours
  3. customAfter the completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionthe residue was dissolved in 5 mL of 1,4-dioxane
  6. additionadded dropwise in a solution of 0.10 g of methoxyamine hydrochloride and 0.10 g of sodium hydroxide in 4 mL of water and 4 mL of acetic acid
  7. additionAfter the completion of the addition dropwise
  8. stirringto stir at room temperature further for 30 minutes
  9. customAfter the completion of the reaction, 10 mL of water
  10. additionwas added in the reaction mixture
  11. extractionextracted with ethyl acetate (40 mL×1)
  12. dry with materialdried over saturated sodium chloride
  13. distillationanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure
  14. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-679e5c2f5e6341909c2ddcdd7821e611
Source dataset
uspto-grants-2015_03
Patent number
US08987464B2

Reaction notes

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