2,5-Dimethylaniline → N-(2,5-dimethylphenyl)-4-methyl-3-oxopentanamide

HRID 1892262

Reaktionsgleichung

Reaktionsgleichung von HRID 1892262
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].[CH3:10][CH:11]([CH3:20])[C:12](=[O:19])[CH2:13][C:14](OCC)=[O:15]>>[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH:4][C:14](=[O:15])[CH2:13][C:12](=[O:19])[CH:11]([CH3:20])[CH3:10]

Komponenten

3

Edukt 2

HCID 72592,5-DimethylanilineHCID 81583Ethyl isobutyrylacetate

Produkt 1

HCID 86669288N-(2,5-dimethylphenyl)-4-methyl-3-oxopentanamide

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 2,5-dimethylaniline (7.70 g, 63.54 mmol) and ethyl 4-methyl-3-oxopentanoate (10.00 g, 1.0 eq) were refluxed at 160° C. overnight. After the reaction mixture was cooled to room temperature, it was triturated with hexane. The resulting precipitate was filtered and dried under high vacuum to yield the desired N-(2,5-dimethylphenyl)-4-methyl-3-oxopentanamide. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 1.18 (d, J=7.03 Hz, 6 H) 2.30 (d, J=7.62 Hz, 6 H) 2.66-2.85 (m, 1 H) 3.64 (s, 2 H) 6.87 (d, J=8.50 Hz, 1 H) 7.06 (d, J=7.62 Hz, 1 H) 7.77 (s, 1 H) 9.13 (br. s., 1 H).

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customit was triturated with hexane
  3. filtrationThe resulting precipitate was filtered
  4. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b3ae5ecf57f947018f8a7e9a6734c8df
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507682B2

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