Nitric Acid → N-[4-Chloro-2-nitro-5-(trifluoromethyl)phenyl]acetamide

HRID 53781

Reaktionsgleichung

Reaktionsgleichung von HRID 53781
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:8]([Cl:11])=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>OS(O)(=O)=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:12]([F:15])([F:13])[F:14])[C:8]([Cl:11])=[CH:9][C:10]=1[N+:16]([O-:18])=[O:17])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 67676n-[4-Chloro-3-(trifluoromethyl)phenyl]acetamide

Produkt 1

HCID 22318004N-[4-Chloro-2-nitro-5-(trifluoromethyl)phenyl]acetamideAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 3-acetamido-6-chlorobenzotrifluoride (908 mg, 3.82 mmol) in concentrated H2SO4 (4 mL) at 0° C. was added dropwise 70% HNO3 (0.5 mL, Baker). The mixture was stirred at 0° C. for 0.5 h, then at room temperature 3 h, and it was poured into ice water (15 g). The precipitate was collected by filtration, affording 990 mg (91%) of crude 3-acetamido-6-chloro-4-nitrobenzotrifluoride. It was crystallized from EtOH/H2O to give 770 mg of pure compound as yellow needles. 1H NMR (CDCl3): δ 2.326 (S, 3H), 8.345 (s, 1H), 9.293 (s, 1H), 10.222 (s, 1H).

Aufarbeitung

  1. filtrationThe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-31bde87f0f284d46921f12823f94862c
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620979

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