Nitric Acid → 4-(Ethylamino)-3-nitrobenzonitrile

HRID 1356699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356699
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([N:7]([CH2:18][CH3:19])S(C2C=CC(C)=CC=2)(=O)=O)=[CH:5][CH:4]=1)#[N:2].[N+:22]([O-])([OH:24])=[O:23]>S(=O)(=O)(O)O>[C:1]([C:3]1[CH:21]=[CH:20][C:6]([NH:7][CH2:18][CH3:19])=[C:5]([N+:22]([O-:24])=[O:23])[CH:4]=1)#[N:2]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 185093134'-Cyano-N-ethyl-p-toluenesulfonanilide

Produkt 1

HCID 31180704-(Ethylamino)-3-nitrobenzonitrileAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

4′-Cyano-N-ethyl-p-toluenesulfonanilide (6.95 g (23.1 mmol) was dissolved in concentrated sulfuric acid (20.0 ml) under cooling with ice. To this, 97% fuming nitric acid (1.00 ml (23.4 mmol)) was added dropwise and the mixture was stirred for 30 minutes under cooling with ice. The resulting mixture was poured into ice-water, followed by extraction with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with ethyl acetate-hexane (1:3) as eluent, to give 1.25 g (28%) of 4-cyano-N-ethyl-2-nitroaniline as yellow crystals.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b153892e567c41bb87388a3462656afe
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586617B1

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