Water → N1-(alpha,alpha,alpha-trifluoro-o-tolyl)-2-chloro-6-fluorobenzhydrazide

HRID 2350936

Reaktionsgleichung

Reaktionsgleichung von HRID 2350936
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[F:12][C:13]([F:23])([F:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][NH2:21].O>N1C=CC=CC=1>[F:12][C:13]([F:22])([F:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]([C:4](=[O:5])[C:3]1[C:7]([F:11])=[CH:8][CH:9]=[CH:10][C:2]=1[Cl:1])[NH2:21]

Komponenten

5

Edukt 3

HCID 962WaterHCID 5208002-(Trifluoromethyl)phenylhydrazineHCID 27365472-Chloro-6-fluorobenzoyl chloride

Produkt 1

HCID 19847775N1-(alpha,alpha,alpha-trifluoro-o-tolyl)-2-chloro-6-fluorobenzhydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

71.7 g (0.37 mol) of 2-chloro-6-fluorobenzoyl chloride are slowly added dropwise to a solution, cooled to 5° C., of 65.4 g (0.37 mol) of o-trifluoromethylphenylhydrazine in 200 ml of pyridine in such a manner that the temperature of the reaction mixture does not exceed 5° C. The mixture is stirred at room temperature for a further 90 minutes and subsequently treated with 400 ml of water. The aqueous phase is extracted three times with 150 ml of diethyl ether each time and the combined organic phases are washed in sequence with 2N sodium hydroxide solution and concentrated sodium chloride solution. The organic phase is then dried over anhydrous sodium sulfate and evaporated under reduced pressure, the crude product being evaporated twice with a small amount of toluene in order to remove excess pyridine. After recrystallization from methylene chloride/n-hexane there is obtained N1 -(α,α,α-trifluoro-o-tolyl)-2-chloro-6-fluorobenzhydrazide, m.p. 147°-148° C.; mass spectrum: 332(19), 157(100).

Aufarbeitung

  1. customdoes not exceed 5° C
  2. extractionThe aqueous phase is extracted three times with 150 ml of diethyl ether each time
  3. washthe combined organic phases are washed in sequence with 2N sodium hydroxide solution and concentrated sodium chloride solution
  4. dry with materialThe organic phase is then dried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customthe crude product being evaporated twice with a small amount of toluene in order
  7. customto remove excess pyridine
  8. customAfter recrystallization from methylene chloride/n-hexane there

Quellen und Nachweise

ORD-Eintrag
ord-8cd88cfd24194cfb877021c8cce7f585
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04871757

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