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

HRID 322214

Reaktionsgleichung

Reaktionsgleichung von HRID 322214
C[OH:2].[NH2:3][OH:4].C1C=NC2C3N=CC=CC=3C=CC=2C=1.[F:19][C:20]1[C:27]([F:28])=[CH:26][CH:25]=[C:24]([C:29]([F:32])([F:31])[F:30])[C:21]=1[C:22]#[N:23]>[Fe](Cl)Cl.CC#N.O>[F:19][C:20]1[C:27]([F:28])=[CH:26][CH:25]=[C:24]([C:29]([F:32])([F:30])[F:31])[C:21]=1[C:22](=[N:3][OH:4])[NH2:23].[F:19][C:20]1[C:27]([F:28])=[CH:26][CH:25]=[C:24]([C:29]([F:32])([F:30])[F:31])[C:21]=1[C:22]([NH2:23])=[O:2]

Komponenten

8

Edukt 4

HCID 787HydroxylamineHCID 887MethanolHCID 13181,10-PhenanthrolineHCID 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 18373917Acetonitrile--water (1/1)Lösungsmittel

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, 99 mg (0.50 mmol) of o-phenanthroline 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. When the reaction solution was analyzed with HPLC [column: Inertsil ODS—34.6 mm ø×250 mm (GL Sciences Inc.), mobile phase; CH3CN—H2O—10% H3PO4 500:500:10 (v/v/v), flow rate; 1.0 ml/min, detection wavelength; 225 nm, and the same conditions for Example 2 and after], it was shown that (I″) (tR 16.0 min) disappeared, 2,3-difluoro-6-trifluoromethylbenzamidoxime (II′) was mainly produced (yield 76.9%, tR 3.6 min) and 2,3-difluoro6-trifluoromethylbenzamide (III′) was produced as a byproduct (yield 8.4%, tR 4.8 min).

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-673a68f0a9b94be4bdf0c65b139088ac
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211232B1

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