Chlorosuccinimide → N-acetyl-N-(5-chloro-2-pyrimidinyl)-2-methyl-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid amide

HRID 552638노트

반응식

HRID 552638 반응식
[C:1]([N:4]([C:17]1[N:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=1)[C:5](=[O:16])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[N:13][OH:14])=[CH:8][C:7]=1[CH3:15])(=[O:3])[CH3:2].ClN1C(=O)CCC1=O.[Cl:32][C:33]1[CH:34]=[C:35]([C:41]([C:43]([F:46])([F:45])[F:44])=[CH2:42])[CH:36]=[C:37]([Cl:40])[C:38]=1[Cl:39].C(=O)([O-])O.[K+]>COCCOC.O>[C:1]([N:4]([C:17]1[N:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=1)[C:5](=[O:16])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:42][C:41]([C:35]3[CH:36]=[C:37]([Cl:40])[C:38]([Cl:39])=[C:33]([Cl:32])[CH:34]=3)([C:43]([F:46])([F:45])[F:44])[O:14][N:13]=2)=[CH:8][C:7]=1[CH3:15])(=[O:3])[CH3:2]

참가 물질

8

반응물 4

HCID 31398ChlorosuccinimideHCID 516893Potassium BicarbonateHCID 498201551,2,3-Trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 86654460N-acetyl-N-(5-chloro-2-pyrimidinyl)-4-hydroxyiminomethyl-2-methyl benzoic acid amide

생성물 1

HCID 86654459N-acetyl-N-(5-chloro-2-pyrimidinyl)-2-methyl-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid amide수율 20.8%

시약·촉매·용매 3

HCID 962Water촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
40 °C

실험 절차

In a solution of 30 mg of N-acetyl-N-(5-chloro-2-pyrimidinyl)-4-hydroxyiminomethyl-2-methyl benzoic acid amide in 5 mL of 1,2-dimethoxyethane, 16 mg of N-chlorosuccinic acid imide was added and stirred at 40° C. for 30 minutes. Then the reaction mixture was left and cooled to room temperature, and 24 mg of 3,4,5-trichloro-1-(1-trifluoromethylethenyl)benzene, 10 mg of potassium hydrogen carbonate and 1 drop of water were added, and continued to stir at room temperature for 1.5 hour. After the completion of the reaction, the reaction mixture was poured in 10 mL of water, and extracted with ethyl acetate (10 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 1:3 to 1:1) to obtain 11 mg of the aimed product as colorless resinous substance.

후처리

  1. waitThen the reaction mixture was left
  2. temperaturecooled to room temperature
  3. stirringto stir at room temperature for 1.5 hour
  4. customAfter the completion of the reaction
  5. extractionextracted with ethyl acetate (10 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

출처 및 근거

ORD 기록
ord-f0565be8fd85402c9d4fa58b20b5af79
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951828B1

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