Nitromethane → (E)-2-(5-(3,4-dichlorophenyl)furan-2-yl)ethenamine

HRID 872447

Reaktionsgleichung

Reaktionsgleichung von HRID 872447
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[N+:16]([CH3:19])([O-])=O.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:15][C:12](/[CH:13]=[CH:19]/[NH2:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

5

Edukt 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 6176885-(3,4-Dichlorophenyl)-2-furaldehyde

Produkt 1

HCID 67170044(E)-2-(5-(3,4-dichlorophenyl)furan-2-yl)ethenamineAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 5-(3,4-dichlorophenyl)furfural (1.18 g, 4.89 mmol) in acetic acid (30 ml) was added nitromethane (0.535 ml, 9.78 mmol) and ammonium acetate (1.13 g, 14.7 mmol). The reaction mixture was heated at 80° C. for 4.5 h. Cooled reaction mixture was poured onto ice water (30 ml) and thus formed precipitate was filtered, washed with water and dried under vacuum to give 1.15 g (83%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 7.37 (d, 1H), 7.43 (d, 1H), 7.76 (d, 1H), 7.95 (dd, 1H), 8.03 (d, 1H), 8.19 (d, 1H), 8.31 (d, 1H).

Aufarbeitung

  1. temperatureCooled
  2. customreaction mixture
  3. additionwas poured onto ice water (30 ml) and thus formed precipitate
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d3ec8c8042a2450380a5863f5cd8d24d
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975254B2

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