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Acetyl chloride → N-acetyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(1-pyrazolyl)benzoic acid amide

HRID 1187952
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1187952
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:29]([F:32])([F:31])[F:30])[O:13][N:12]=[C:11]([C:14]3[CH:27]=[CH:26][C:17]([C:18]([NH:20][N:21]4[CH:25]=[CH:24][CH:23]=[N:22]4)=[O:19])=[C:16]([CH3:28])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Na+].[H][H].[C:37](Cl)(=[O:39])[CH3:38]>O1CCCC1>[C:37]([N:20]([N:21]1[CH:25]=[CH:24][CH:23]=[N:22]1)[C:18](=[O:19])[C:17]1[CH:26]=[CH:27][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)([C:29]([F:30])([F:32])[F:31])[O:13][N:12]=2)=[CH:15][C:16]=1[CH3:28])(=[O:39])[CH3:38]
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Komponenten

6

Edukt 4

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 671639784-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(1-pyrazolyl)benzoic acid amideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 67164590N-acetyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methyl-N-(1-pyrazolyl)benzoic acid amide
Ausbeute 26,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a solution of 0.20 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(1-pyrazolyl)benzoic acid amide in 3 mL of tetrahydrofuran, 0.027 g of 60% oily sodium hydride was added and stirred at room temperature for 10 minutes. After ceasing the generation of hydrogen gas, 0.049 g of acetyl chloride was added under cooling with ice and with stirring, and continued to stir at the same temperature further for 10 minutes. After the completion of the reaction, the reaction mixture was poured in 10 mL of ice water, extracted with ethyl acetate (10 mL×1), the organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and 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 0.058 g of the aimed product as yellow resinous substance.

Aufarbeitung

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringwith stirring
  4. stirringto stir at the same temperature further for 10 minutes
  5. customAfter the completion of the reaction
  6. extractionextracted with ethyl acetate (10 mL×1)
  7. dry with materialdried over saturated sodium chloride aqueous solution
  8. distillationanhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure
  9. customThe residue was purified with silica gel column chromatography that

Quellen und Nachweise

ORD-Eintrag
ord-59540bc95f08413a8cd099ee5f4489b0
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08673951B2

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