Hydrochloric Acid → 3-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenylhydrazine
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:21]([F:24])([F:23])[F:22])[O:13][N:12]=[C:11]([C:14]3[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=3)[NH2:17])[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[N:26]([O-])=O.[Na+].[Sn](Cl)Cl.[OH-].[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:21]([F:22])([F:24])[F:23])[O:13][N:12]=[C:11]([C:14]3[CH:15]=[C:16]([NH:17][NH2:26])[CH:18]=[CH:19][CH:20]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
In 1,4-dioxane (4 mL), 3-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]aniline (1.0 g) was dissolved, and thereto was added a concentrated hydrochloric acid (7 mL) at room temperature. After stirring at the same temperature for 20 minutes, this solution was cooled to 0° C., and thereto was added a solution of sodium nitrite (184 mg) in water (4 mL), and the mixture was stirred at the same temperature for 15 minutes. To this reaction solution was added dropwise a solution of tin(II) chloride (1.11 g) in a concentrated hydrochloric acid (2 ml). The reaction mixture was neutralized with 2N sodium hydroxide. The aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain crude 3-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenylhydrazine (1.0 g).
Aufarbeitung
- stirringthe mixture was stirred at the same temperature for 15 minutes
- extractionThe aqueous layer was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-2a3a55a3480a450c81cf6c5d89c83129
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08785485B2
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