Chlorosuccinimide → methyl N-[2-methyl-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoyl]carbamate

HRID 552669ノート

反応式

HRID 552669 の反応式
[OH:1][N:2]=[CH:3][C:4]1[CH:16]=[CH:15][C:7]([C:8]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[O:9])=[C:6]([CH3:17])[CH:5]=1.ClN1C(=O)CCC1=O.[Cl:26][C:27]1[CH:28]=[C:29]([C:35]([C:37]([F:40])([F:39])[F:38])=[CH2:36])[CH:30]=[C:31]([Cl:34])[C:32]=1[Cl:33].C(=O)([O-])O.[K+]>COCCOC.O>[CH3:17][C:6]1[CH:5]=[C:4]([C:3]2[CH2:36][C:35]([C:29]3[CH:30]=[C:31]([Cl:34])[C:32]([Cl:33])=[C:27]([Cl:26])[CH:28]=3)([C:37]([F:40])([F:39])[F:38])[O:1][N:2]=2)[CH:16]=[CH:15][C:7]=1[C:8]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[O:9]

参加物

8

反応物 4

HCID 31398ChlorosuccinimideHCID 516893Potassium BicarbonateHCID 498201551,2,3-Trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 86654469methyl N-[4-hydroxyiminomethyl-2-methylbenzoyl]carbamate

生成物 1

HCID 86654471methyl N-[2-methyl-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoyl]carbamate収率 23.7%

試薬・触媒・溶媒 3

HCID 962Water触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
60 °C

実験手順

In a solution of 45 mg of methyl N-[4-hydroxyiminomethyl-2-methylbenzoyl]carbamate in 10 mL of 1,2-dimethoxyethane, 40 mg of N-chlorosuccinimide was added, and stirred at 60° C. for 45 minutes. Then, the reaction mixture was left and cooled to room temperature, and then 68 mg of 3,4,5-trichloro-1-(1-trifluoromethylethenyl)benzene, 40 mg of potassium hydrogen carbonate and 5 drops of water were added, and continued to stir at room temperature further for 15 hour. After the completion of the reaction, the reaction mixture was poured in 10 mL of water, and extracted with ethyl acetate (15 mL×2). The combined organic phases were dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (gradient of 1:2 to 1:1) to obtain 23 mg of the aimed product as colorless resinous substance.

後処理

  1. waitThen, the reaction mixture was left
  2. temperaturecooled to room temperature
  3. stirringto stir at room temperature further for 15 hour
  4. customAfter the completion of the reaction
  5. extractionextracted with ethyl acetate (15 mL×2)
  6. dry with materialdried over saturated sodium chloride aqueous solution
  7. distillationanhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure
  8. customThe residue was purified with silica gel column chromatography that

出典と根拠

ORDレコード
ord-768687e620f94a0799441e6e68ff6992
出典データセット
uspto-grants-2011_05
特許番号
US07951828B1

反応ノート

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