Nitric Acid → HCID 178418771, Verbindung

HRID 8502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 8502
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[N:16]#[C:17][NH2:18].[N+:19]([O-:22])([OH:21])=[O:20].CCOCC>C(O)C>[N+:19]([O-:22])([O-:21])=[O:20].[C:5]([C:4]1[CH:3]=[C:2]([NH:1][C:17]([NH2:18])=[NH2+:16])[CH:15]=[CH:14][CH:13]=1)(=[O:6])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 944Nitric Acid2×HCID 3283Diethyl EtherHCID 9864Cyanamide2×HCID 17817Methanone, (3-aminophenyl)phenyl-

Produkt 1

HCID 178418771HCID 178418771, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a room temperature solution of 3-aminobenzophenone (4.0 g, 20.2 mmol) in ethanol (50 mL) was added cyanamide (1.8 mL 50 wt % in water, 23.3 mmol) followed by the dropwise addition of concentrated nitric acid (1.42 mL). The mixture was heated at reflux for 2 hours and then additional cyanamide (1.8 mL, 50 wt % in water, 23.3 mmol) and nitric acid (1.42 mL) were added. The mixture was heated for an additional 1 hour then allowed to cool to room temperature. Ether was added and the precipitate collected on a filter. This material was recrystallized fromethyl acetate/methanol/ether to yield N-(3-benzoylphenyl)guanidinium nitrate (2.5 g, 41%) as a white crystalline solid. 1H NMR (DMSO-d6): δ 9.75 (s, 1 H), 7.76 (d, 2 H), 7.69 (t, 1 H), 7.61 (d, 2 H), 7.58–7.49 (m, 9 H); 13C NMR (DMSO-d6): δ 195.01, 155.76, 138.31, 136.65, 135.80, 132.99, 130.05, 129.71, 128.67, 128.44, 127.39, 125.34; MS m/z 240 (M+1 of free base).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe mixture was heated for an additional 1 hour
  4. customthe precipitate collected on a filter
  5. customThis material was recrystallized fromethyl acetate/methanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-87029d2911b1461884aaf8aea8da9ffd
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087618B2

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