Hydrogen Peroxide → N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-2,4,5-trifluoro-benzamide

HRID 1943119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943119
[NH2:1][C:2]1[C:3]([F:31])=[C:4]([CH:26]=[C:27]([F:30])[C:28]=1[F:29])[C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[CH3:25])=[O:6].FC(F)(F)C(O)=[O:35].OO.[OH2:41]>C(Cl)(Cl)Cl>[CH3:25][C:9]1[CH:10]=[C:11]([C:15]([F:24])([C:20]([F:21])([F:22])[F:23])[C:16]([F:18])([F:19])[F:17])[CH:12]=[C:13]([CH3:14])[C:8]=1[NH:7][C:5](=[O:6])[C:4]1[CH:26]=[C:27]([F:30])[C:28]([F:29])=[C:2]([N+:1]([O-:35])=[O:41])[C:3]=1[F:31]

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 6422Trifluoroacetic acidHCID 592269383-amino-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2,4,5-trifluoro-benzamide

Produkt 1

HCID 59226973N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-2,4,5-trifluoro-benzamideAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of 3-amino-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2,4,5-trifluoro-benzamide (32.8 g, 71 mmol) (Example I14) and trifluoro-acetic acid (237 ml) in chloroform (118 ml) was added drop-wise aqueous hydrogen peroxide (67 ml) (35% w/v). The reaction mixture was kept at approximately 50° C. with external cooling. The reaction mixture was stirred at 55° C. for 30 minutes, then poured onto a mixture of ice and water. The mixture was extracted twice with dichloromethane. The combined organic phases were washed with aqueous sodium hydrogen carbonate (1M), dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 7:3) to give N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-2,4,5-trifluoro-benzamide (23.94 g, 68.5% yield). 1H-NMR (400 MHz, CDCl3): 2.35 (6H, s), 7.38 (2H, s), 7.68 (1H, d), 8.25 (1H, m) ppm.

Aufarbeitung

  1. customwas kept at approximately 50° C. with external cooling
  2. extractionThe mixture was extracted twice with dichloromethane
  3. washThe combined organic phases were washed with aqueous sodium hydrogen carbonate (1M)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-8991518d60054a83b632a678b8006d4e
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389766B2

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