Ethyl Acetate → HCID 86611475, compound

HRID 1096129Notes

Reaction equation

HRID 1096129 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:28]=[CH:27][C:17]([C:18]([NH:20][CH2:21][CH:22](OC)OC)=[O:19])=[C:16]([CH3:29])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[CH3:35][O:36][NH2:37].C(OCC)(=O)C>CO.O>[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:28]=[CH:27][C:17]([C:18]([NH:20][CH2:21][CH:22]=[N:37][O:36][CH3:35])=[O:19])=[C:16]([CH3:29])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 66785224HCID 66785224, compound

Product 1

HCID 86611475HCID 86611475, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

In a solution of 152 mg of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2-dimethoxyethyl) -2-methyl benzoic acid amide (Compound of the present invention No. 5-083) synthesized similarly to Synthetic Example 5 in 14 ml of methanol-water (6:1) mixed solvent, 38 mg of methoxyamine hydrochloride was added, and stirred under reflux with heat for 8 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, diluted by adding 80 ml of ethyl acetate, washed with water (30 ml×2), and 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 ethylacetate-hexane (1:1), and 102 mg of the aimed product was obtained as colorless resinous substance.

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. temperaturewith heat for 8 hours
  4. customAfter the completion of the reaction
  5. waitthe reaction mixture was left
  6. additiondiluted
  7. washwashed with water (30 ml×2)
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-39dff67df33d473f99a2335b0d18a415
Source dataset
uspto-grants-2012_03
Patent number
US08138213B2

Reaction notes

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