4-(Diethylamino)benzaldehyde → HCID 178463809, Verbindung

HRID 431717

Reaktionsgleichung

Reaktionsgleichung von HRID 431717
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].[CH2:13]([N:15]([CH2:24][CH3:25])[C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)[CH3:14]>[N+](C1C=CC=CC=1)([O-])=O>[CH2:13]([N:15]([C:16]1[CH:17]=[CH:18][C:19]([C:20]2[NH:12][C:11]3[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=3[N:1]=2)=[CH:22][CH:23]=1)[CH2:24][CH3:25])[CH3:14]

Komponenten

4

Edukt 2

HCID 671144-(Diethylamino)benzaldehydeHCID 1355243,5-Diamino-2-methylbenzoic acid

Produkt 1

HCID 178463809HCID 178463809, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7416NitrobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

Methyl 3,4-diaminobenzoate (0.73 g, 4.42 mmol), 4-(diethylamino)benzaldehyde (3.0 g, 16.9 mmol) were dissolved in nitrobenzene (30 mL) and refluxed on a 145° C. oil bath overnight. The nitrobenzene was then removed in vacuo using a Kugelrohr apparatus (60° C., 0.1 mm Hg). The remaining oily residue was dissolved in CHCl3 and washed with water (3×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The crude oil was then purified through colurnn chromatography using a solvent system of 1% MeOH/CHCl3 to give methyl 2-(4-(N,N-diethyl)aminophenyl)benzimidazole-6-carboxylate as a yellowish solid (1.17 g, 82% yield). TLC (2.5% MeOH/CHCl3) Rf=0.26; 1H-NMR (500 MHz, CDCl3) 9.87 (s br, 1H), 8.30 (s br, 1H), 7.94 (dd, 1.5, 8.5, 1H), 7.91 (d, 8.5, 2H), 7.60 (s br, 1H), 6.72 (d, 8.5, 2H), 3.42 (q, 7.0, 4H), 1.21 (t, 7.0, 6H); IR (neat) 3508, 2063, 2920, 1712, 1611, 1504, 1434, 1360, 1307, 1269, 1205, 1157, 1082, 1008, 821, 751.

Aufarbeitung

  1. customThe nitrobenzene was then removed in vacuo
  2. customa Kugelrohr apparatus (60° C., 0.1 mm Hg)
  3. dissolutionThe remaining oily residue was dissolved in CHCl3
  4. washwashed with water (3×50 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude oil was then purified through colurnn chromatography

Quellen und Nachweise

ORD-Eintrag
ord-468ef4aa63f642c78e6e003b0413293d
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660742B2

Verknüpfte Notizen

Wird geladen…