6-Nitro-m-toluidine → Isopropylidene (5-methyl-2-nitroanilino)methylenemalonate

HRID 613562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 613562
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[CH3:12][C:13]1([CH3:21])[O:18][C:17](=[O:19])[CH2:16][C:15](=[O:20])[O:14]1.[CH:22](OCC)(OCC)OCC>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH:7][CH:22]=[C:16]1[C:17](=[O:19])[O:18][C:13]([CH3:21])([CH3:12])[O:14][C:15]1=[O:20]

Komponenten

5

Edukt 3

HCID 113566-Nitro-m-toluidineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformate

Produkt 1

HCID 53705573Isopropylidene (5-methyl-2-nitroanilino)methylenemalonateAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel3×

Versuchsvorschrift

To a stirred suspension of 5-methyl-2-nitroaniline (10.0 g) in ethanol (20 ml) were added 2,2-dimethyl-1,3-dioxane-4,6-dione (9.95 g) and triethyl orthoformate (10.7 g) at 50° C. The resulting mixture was heated at 120° C. for one hour during which time ethanol (20 ml) was added to the mixture and ethanol liberated was distilled off. After cooling, ethyl acetate (40 ml) was added thereto and the resulting precipitate was collected by filtration. The solid was washed with hot ethanol (40 ml) and allowed to cool to ambient temperature. The precipitate was collected by filtration and air-dried to afford isopropylidene (5-methyl-2-nitroanilino)methylenemalonate (15.2 g) as yellow needles.

Aufarbeitung

  1. distillationliberated was distilled off
  2. temperatureAfter cooling
  3. additionethyl acetate (40 ml) was added
  4. filtrationthe resulting precipitate was collected by filtration
  5. washThe solid was washed with hot ethanol (40 ml)
  6. filtrationThe precipitate was collected by filtration
  7. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-caf00fac7d5440259ad637ff373070c2
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06008230

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