Chlorosuccinimide → N-[(4-{5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl}naphthalen-1-yl)methyl]acetamide

HRID 386750노트

반응식

HRID 386750 반응식
ClN1C(=O)CCC1=O.[OH:9][N:10]=[CH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])=[CH:14][CH:13]=1.[Cl:27][C:28]1[CH:33]=[C:32]([C:34]([C:36]([F:39])([F:38])[F:37])=[CH2:35])[CH:31]=[C:30]([C:40]([F:43])([F:42])[F:41])[C:29]=1[Cl:44].C(=O)(O)[O-].[K+]>CN(C)C=O.O>[Cl:27][C:28]1[CH:33]=[C:32]([C:34]2([C:36]([F:39])([F:37])[F:38])[O:9][N:10]=[C:11]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])=[CH:14][CH:13]=3)[CH2:35]2)[CH:31]=[C:30]([C:40]([F:41])([F:42])[F:43])[C:29]=1[Cl:44]

참가 물질

7

반응물 4

HCID 31398ChlorosuccinimideHCID 516893Potassium BicarbonateHCID 86643383N-({4-[(hydroxyimino)methyl]naphthalen-1-yl}methyl)acetamideHCID 866433841,2-Dichloro-3-(trifluoromethyl)-5-[1-(trifluoromethyl)ethenyl]benzene

생성물 1

HCID 86643382N-[(4-{5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl}naphthalen-1-yl)methyl]acetamide수율 44.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

N-chlorosuccinimide (0.06 g) was added to N-({4-[(hydroxyimino)methyl]naphthalen-1-yl}methyl)acetamide (0.1 g) in N,N-dimethylformamide (10 ml), and the reaction mixture was stirred at room temperature for 2 hours. 1,2-dichloro-3-(trifluoromethyl)-5-[1-(trifluoromethyl)ethenyl]benzene (0.75 g) and potassium bicarbonate (0.13 g) was added to the reaction mixture, and the mixture was stirred at room temperature for 8 hours. Water was poured into the reaction mixture, and it was extracted with ethyl acetate. The organic layer was washed with brine, and dried over Magnesium sulfate anhydrous. The solvent was evaporated under the reduced pressure, and the residue was purified with silicagel columnchromatography to get N-[(4-{5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl}naphthalen-1-yl)methyl]acetamide (0.1 g).

후처리

  1. stirringthe mixture was stirred at room temperature for 8 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Magnesium sulfate anhydrous
  5. customThe solvent was evaporated under the reduced pressure
  6. customthe residue was purified with silicagel columnchromatography

출처 및 근거

ORD 기록
ord-c5e5592a02704878b3088e267fa1fa98
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372867B2

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