Sulfuric Acid → 3,5-Dinitroaniline

HRID 76768

Reaktionsgleichung

Reaktionsgleichung von HRID 76768
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)C(O)=O)([O-:3])=[O:2].S(=O)(=O)(O)O.[N-:21]=[N+]=[N-].[Na+]>C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[NH2:21])([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 1118Sulfuric Acid2×HCID 74333,5-Dinitrobenzoic acidHCID 33557Sodium Azide

Produkt 1

HCID 120683,5-Dinitroaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3,5-dinitrobenzoic acid (4.0 g, 18.9 mmol) in a mixture of concentrated sulfuric acid (6 mL), 30% fuming sulfuric acid (18 mL) and CHCl3 (25 mL) was added sodium azide (1.4 g, 21.7 mmol), in small portions. The resulting mixture was heated to reflux (80° C.) for 3 hours and then cooled to 25° C. after which it was poured on ice. An orange solid was isolated after vacuum filtration (3.25 g, 17.7 mmol, 94%). 1H NMR (300 MHz, CDCl3) δ 8.14 (t, J=1.8 Hz, 1H), 7.64 (d, J=1.8 Hz, 2H), 4.39 (s (br), 2H); 13C NMR (75 MHz, CDCl3) δ 151.9, 150.1, 113.1, 105.2; HRMS (ESI) Calculated for C6H4N3O4 [M−H]−: 182.0195. Found: 182.0207. m.p.: 113.1° C.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperaturecooled to 25° C. after which it
  3. additionwas poured on ice
  4. customAn orange solid was isolated
  5. filtrationafter vacuum filtration (3.25 g, 17.7 mmol, 94%)

Quellen und Nachweise

ORD-Eintrag
ord-fa9084e724d143b2874a025815fb3b88
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835641B2

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