Water → 2-Methyl-N-(3-methyl-4-nitrophenyl)acrylamide

HRID 133729

Reaktionsgleichung

Reaktionsgleichung von HRID 133729
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[NH2:5].[C:12](Cl)(=[O:16])[C:13]([CH3:15])=[CH2:14].O>CN(C)C(=O)C>[CH3:15][C:13](=[CH2:14])[C:12]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:2]([CH3:1])[CH:3]=1)=[O:16]

Komponenten

5

Edukt 3

HCID 962WaterHCID 118984-Nitro-m-toluidineHCID 13528Methacryloyl chloride

Produkt 1

HCID 450976432-Methyl-N-(3-methyl-4-nitrophenyl)acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

3-Methyl-4-nitroaniline (2.0 g, 13 mmol) in N,N-dimethylacetamide (DMAC) (6 ml) was added dropwise to a cooled solution of methacryloyl chloride (2.0 ml, 20.7 mmol) in a nitrogen atmosphere while the temperature of the reaction mixture was maintained between 0-5° C. The solution was allowed to warm to room temperature and the mixture was stirred over night. The mixture was poured into water (70 ml) and extracted with ethyl acetate (4×40 ml). The organic phase was washed with saturated Na2CO3 (3×20 ml) and water (1×50 ml), dried over Na2SO4 and evaporated. The yield of the crude product was 4.17 g (contains DMA, theoretical yield 2.9 g), and it was used without further purifications. 1H NMR (DMSO-d6): 1.97 (3H, s), 2.55 (3H, s), 5.62 (1H, m), 5.96 (1H, m), 7.80 (2H, m), 8.05 (1H, m), 10.22 (1H, s).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. extractionextracted with ethyl acetate (4×40 ml)
  3. washThe organic phase was washed with saturated Na2CO3 (3×20 ml) and water (1×50 ml)
  4. dry with materialdried over Na2SO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-14257930e63c499bab077596c16d2683
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390923B2

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