Hydroxylamine → 2,3-Difluoro-6-(trifluoromethyl)benzamide

HRID 322216

Reaktionsgleichung

Reaktionsgleichung von HRID 322216
[NH2:1][OH:2].[F:3][C:4]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]([C:13]([F:16])([F:15])[F:14])[C:5]=1[C:6]#[N:7]>[Fe](Cl)Cl.CO>[F:3][C:4]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]([C:13]([F:16])([F:14])[F:15])[C:5]=1[C:6](=[N:1][OH:2])[NH2:7].[F:3][C:4]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]([C:13]([F:16])([F:14])[F:15])[C:5]=1[C:6]([NH2:7])=[O:2]

Komponenten

6

Edukt 2

HCID 787HydroxylamineHCID 101044562,3-Difluoro-6-(trifluoromethyl)benzonitrile

Produkt 2

HCID 220101192,3-Difluoro-6-(trifluoromethyl)benzamideHCID 544182132,3-Difluoro-N-hydroxy-6-(trifluoromethyl)benzimidamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24458Ferrous ChlorideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

In a colorless, transparent glass reaction vessel was placed a mixed solvent of 150 ml of methanol-distilled water (volume ratio 1:2) into which were dissolved beforehand 9.91 g (150 mmol) of 50% hydroxylamine aqueous solution and on purpose 86 μg (0.00068 mmol) of iron(II) chloride. Into the mixed solvent was added 10.36 g (50.0 mmol) of 2,3-difluoro-6-trifluoromethylbenzonitrile (I″). The reaction temperature stood at 60° C. for 6 hours and was returned to room temperature. In HPLC analysis of the reaction solution, it was shown that (I″) disappeared, 2,3-difluoro-6-trifluoromethylbenzamidoxime (II′) was mainly produced (yield 62.4%) and 2,3-difluoro-6-trifluoromethylbenzamide (III′) was noticeably produced as a byproduct (yield 22.8%).

Aufarbeitung

  1. customIn a colorless, transparent glass reaction vessel
  2. distillationdistilled water (volume ratio 1:2) into which
  3. customwas returned to room temperature

Quellen und Nachweise

ORD-Eintrag
ord-5267a7ccf8004844acdb99cd63e39033
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211232B1

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