Nitroethane → 1-Chloro-2-nitro-4-[(1E)-2-nitro-1-propen-1-yl]benzene

HRID 2382610Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382610
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[Cl:12])[CH:7]=O)([O-:3])=[O:2].C([O-])(=O)C.[NH4+].[N+:18]([CH2:21][CH3:22])([O-:20])=[O:19]>C(Cl)Cl>[Cl:12][C:11]1[CH:10]=[CH:9][C:6](/[CH:7]=[C:21](/[N+:18]([O-:20])=[O:19])\[CH3:22])=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 6587NitroethaneHCID 855054-Chloro-3-nitrobenzaldehydeHCID 517165Ammonium Acetate

Produkt 1

HCID 137762661-Chloro-2-nitro-4-[(1E)-2-nitro-1-propen-1-yl]benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A stirred mixture of 3-Nitro-4-chlorobenzaldehyde (10 g, 53.89 mmol), ammonium acetate (1.39 g, 18 mmol) and nitroethane (31.3 ml, 432 mmol) is heated at reflux (80° C.) overnight. After cooling to room temperature the reaction mixture is concentrated if vacuo to give a solid which is dissolved in DCM (200 ml) and washed with water (3×200 ml), followed by brine (200 ml). The organic portion is dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as an orange solid.

Aufarbeitung

  1. temperatureis heated
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. concentrationis concentrated if vacuo
  4. customto give a solid which
  5. washwashed with water (3×200 ml)
  6. dry with materialThe organic portion is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d01c4645e48d4893b364a106fc13dade
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263585B2

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