Nitric Acid → HCID 178419082, Verbindung

HRID 896771

Reaktionsgleichung

Reaktionsgleichung von HRID 896771
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].[N:14]#[C:15][NH2:16].[N+:17]([O-:20])([OH:19])=[O:18]>C(O)C>[N+:17]([O-:20])([O-:19])=[O:18].[CH3:13][O:12][C:8]1[CH:7]=[C:5]([NH:6][C:15]([NH2:16])=[NH2+:14])[CH:4]=[C:3]([O:2][CH3:1])[C:9]=1[O:10][CH3:11]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 9864CyanamideHCID 322853,4,5-Trimethoxyaniline

Produkt 1

HCID 178419082HCID 178419082, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a room temperature solution of 3,4,5-trimethoxyaniline (3.46 g, 18.9 mmol) in ethanol (20 mL) was added cyanamide (1.68 mL 50 wt % in water, 21.7 mmol) followed by the dropwise addition of concentrated nitric acid (1.33 mL). The mixture was heated at reflux for 13 hours and allowed to cool to room temperature. The mixture was concentrated in vacuo to approximately 70% of its original volume and ether was added. The resulting precipitate was isolated on a filter to yield N-(3,4,5-trimethoxyphenyl) guanidinium nitrate (2.5 g, 46%) as a grey powder. 1H NMR (DMSO-d6): δ 9.47 (s, 1 H), 7.29 (s, 3 H), 6.57 (s, 2 H), 3.80 (s, 6 H), 3.68 (s, 3 H); 13C NMR (DMSO-d6): δ 155.78, 153.33, 136.07, 130.58, 102.90, 59.99, 55.96; MS m/z 226 (M+1 of free base).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 13 hours
  3. concentrationThe mixture was concentrated in vacuo to approximately 70% of its original volume and ether
  4. additionwas added
  5. customThe resulting precipitate was isolated on
  6. filtrationa filter

Quellen und Nachweise

ORD-Eintrag
ord-613e8bfc479d4de990e1b75f7072fc4d
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919352B2

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