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

HRID 386750ノート

反応式

HRID 386750 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c5e5592a02704878b3088e267fa1fa98
出典データセット
uspto-grants-2013_02
特許番号
US08372867B2

反応ノート

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