Sodium Hydroxide → 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(ethoxyimino-methyl)-2-methyl benzoic acid amide

HRID 1187981Notes

Reaction equation

HRID 1187981 reaction equation
Cl.[CH2:2]([O:4]N)[CH3:3].[OH-].[Na+].O1CCOCC1.[Cl:14][C:15]1[CH:16]=[C:17]([C:22]2([C:41]([F:44])([F:43])[F:42])[O:26][N:25]=[C:24]([C:27]3[CH:39]=[CH:38][C:30]([C:31]([N:33]=[CH:34][N:35](C)C)=[O:32])=[C:29]([CH3:40])[CH:28]=3)[CH2:23]2)[CH:18]=[C:19]([Cl:21])[CH:20]=1>O.C(O)(=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([C:22]2([C:41]([F:44])([F:43])[F:42])[O:26][N:25]=[C:24]([C:27]3[CH:39]=[CH:38][C:30]([C:31]([NH:33][CH:34]=[N:35][O:4][CH2:2][CH3:3])=[O:32])=[C:29]([CH3:40])[CH:28]=3)[CH2:23]2)[CH:18]=[C:19]([Cl:21])[CH:20]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 76850O-ethylhydroxylamine hydrochlorideHCID 547675024-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl]-N-[(dimethylamino)methylene]-2-methylbenzamide

Product 1

HCID 1363378154-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(ethoxyimino-methyl)-2-methyl benzoic acid amideYield 68.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

in a solution of 0.25 g of ethoxyamine hydrochloride in 4 mL of water and 8 mL of acetic acid, a solution of 0.20 g of sodium hydroxide in 4 mL of water was added, and then 5 mL of 1,4-dioxane solution of 0.62 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-N-(dimethyl-aminomethylidene)-2-methyl benzamide synthesized in Synthetic Example 30 was added dropwise at room temperature with stirring. After the completion of the addition dropwise, it was continued to stir at the same temperature further for 2 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, 50 mL of ethyl acetate was added in the residue, and washed with water. The organic phase was dehydrated with and dried over saturated sodium chloride and then anhydrous sodium sulfate, 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 0.44 g of the aimed product as white crystal. Melting point 143.0 to 146.0° C.

Workup

  1. additionwas added dropwise at room temperature
  2. additionAfter the completion of the addition dropwise
  3. stirringto stir at the same temperature further for 2 hours
  4. customAfter the completion of the reaction
  5. distillationthe solvent was distilled off under reduced pressure, 50 mL of ethyl acetate
  6. additionwas added in the residue
  7. washwashed with water
  8. dry with materialdried over saturated sodium chloride
  9. distillationanhydrous sodium sulfate, the solvent was distilled off under reduced pressure
  10. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-0c846fe212504b01bb8bfd6487f93011
Source dataset
uspto-grants-2014_03
Patent number
US08673951B2

Reaction notes

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