Nitric Acid → 1-Acetamido-2-nitro-3,5-bis(trifluoromethyl)benzene

HRID 439524

Reaktionsgleichung

Reaktionsgleichung von HRID 439524
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[CH:6]=1)(=[O:3])[CH3:2].[N+:19]([O-])([OH:21])=[O:20]>OS(O)(=O)=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:15]([F:16])([F:17])[F:18])[CH:8]=[C:9]([C:11]([F:13])([F:14])[F:12])[C:10]=1[N+:19]([O-:21])=[O:20])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 7236003',5'-Bis(trifluoromethyl)acetanilide

Produkt 1

HCID 199585741-Acetamido-2-nitro-3,5-bis(trifluoromethyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1-acetamido-3,5-bis(trifluoromethyl)benzene (400 mg, 1.37 mmol) in concentrated H2SO4 (3 mL) at 0° C. was added dropwise 70% HNO3 (0.4 mL, Baker). The mixture was stirred at 0° C. for 0.5 h, then at room temperature for 3 h and it was poured into ice water (10 g). The precipitate was collected by filtration, affording 400 mg of crude product which contained two compounds by 1H NMR. It was separated on a column of silica gel, eluted with chloroform, to afford 134 mg of pure 1-acetamido-2-nitro-3,5-bis(trifluoromethyl)benzene as white long needles. mp: 190°-2° C., 1H NMR (CDCl3): δ2.226 (s, 3H), 7.765 (s, 1H), 7.978 (s, 1H); 8.918 (s, 1H).

Aufarbeitung

  1. waitat room temperature for 3 h
  2. filtrationThe precipitate was collected by filtration
  3. customaffording 400 mg of crude product which
  4. customIt was separated on a column of silica gel
  5. washeluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-055b6a44d5624394855b79eefdce8a77
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05514680

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