Nitric Acid → 2,2,2-Trifluoro-N-[2-(4-methoxy-3-nitrophenyl)ethyl]acetamide

HRID 1648883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1648883
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)=[O:4].[N+:18]([O-])([OH:20])=[O:19]>FC(F)(F)C(O)=O>[F:1][C:2]([F:16])([F:17])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([N+:18]([O-:20])=[O:19])[CH:9]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 8856202,2,2-trifluoro-N-[2-(4-methoxyphenyl)ethyl]acetamide

Produkt 1

HCID 128075402,2,2-Trifluoro-N-[2-(4-methoxy-3-nitrophenyl)ethyl]acetamideAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel2×

Versuchsvorschrift

To a solution of 30 g (0.121 mole) of the amide in 254 ml of trifluoroacetic acid at 0° under an argon atmosphere was added dropwise with stirring a solution of 7.5 ml (0.12 mole) of conc. nitric acid in 56 ml of trifluoroacetic acid. The reaction mixture was stirred at 0° for 1/2 hour and at room temperature for 2 hours. The solvents were evaporated. The residue was dissolved in ethyl acetate which was extracted with 5% hydrochloric acid, dilute sodium bicarbonate solution and brine, then dried over anhydrous magnesium sulfate and activated charcoal. After filtering, the solvents were removed to give 34.8 g (98%) of crude (2-trifluoroacetamidoethyl)-3-nitro-4-methoxybenzene which was an amber-colored solid. This material was recrystallized from 400 ml of 1:3 ethyl acetatehexane to give 25.3 g (71.5%) of the product, m.p. 92.5°-93.0°. The mother liquors were concentrated and recrystallized to give a second crop, 4.59 g (13 %), m.p. 90°-92° C.

Aufarbeitung

  1. customThe solvents were evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate which
  3. extractionwas extracted with 5% hydrochloric acid, dilute sodium bicarbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate and activated charcoal
  5. filtrationAfter filtering
  6. customthe solvents were removed

Quellen und Nachweise

ORD-Eintrag
ord-ee5cdb4266524e0ba3cf7c19cbceea89
Quelldatensatz
uspto-grants-1983_11
Patentnummer
US04414224

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