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

HRID 1187981노트

반응식

HRID 1187981 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0c846fe212504b01bb8bfd6487f93011
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673951B2

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