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Triethylamine → 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide

HRID 1844805
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1844805
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2([C:30]([F:33])([F:32])[F:31])[O:20][N:19]=[C:18]([C:21]3[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=3)[CH2:17]2)[CH:12]=[C:13]([Cl:15])[CH:14]=1.[F:34][C:35]([F:39])([F:38])[CH2:36][NH2:37]>C(Cl)(Cl)Cl.O>[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2([C:30]([F:33])([F:32])[F:31])[O:20][N:19]=[C:18]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([NH:37][CH2:36][C:35]([F:39])([F:38])[F:34])=[O:26])=[CH:23][CH:22]=3)[CH2:17]2)[CH:12]=[C:13]([Cl:15])[CH:14]=1
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 871502064-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] benzoic acid chloride

Produkt 1

HCID 113406964-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amideAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

In a solution of 0.29 g of 2,2,2-trifluoroethylamine and 0.37 g of triethylamine in 20 ml of chloroform, 1.81 g of the crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] benzoic acid chloride dissolved in 10 ml of chloroform was added dropwise with cooling with ice and with stirring. After the completion of addition dropwise, the mixture was continued to stir at room temperature further for 30 minutes. After the completion of the reaction, the reaction mixture was poured in 100 ml of water, and extracted with chloroform (20 ml×3), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and passed through a glass filter packed with silica gel, and then the solvent was distilled off under reduced pressure. The residual solid was washed with hexane to obtain 1.05 g of the aimed product as white crystal.

Aufarbeitung

  1. additionwas added dropwise
  2. temperaturewith cooling with ice
  3. additionAfter the completion of addition dropwise
  4. stirringto stir at room temperature further for 30 minutes
  5. customAfter the completion of the reaction
  6. extractionextracted with chloroform (20 ml×3)
  7. washthe organic phase was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfilter
  10. distillationthe solvent was distilled off under reduced pressure
  11. washThe residual solid was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-6fc7613562cc4950aa2e3decb5017489
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08946492B2

Notizen zur Reaktion

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