Dimethylformamide dimethyl acetal → N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methyl-methanesulfonamide

HRID 550557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 550557
[C:1]([C:4]1[CH:5]=[C:6]([N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].CO[CH:18](OC)[N:19]([CH3:21])[CH3:20]>C(OCC)(=O)C.CO>[CH3:18][N:19]([CH3:21])[CH:20]=[CH:2][C:1]([C:4]1[CH:5]=[C:6]([N:10]([CH3:15])[S:11]([CH3:14])(=[O:12])=[O:13])[CH:7]=[CH:8][CH:9]=1)=[O:3]

Komponenten

4

Edukt 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67199578n-(3-Acetyl-phenyl)-n-methyl-methanesulfonamide

Produkt 1

HCID 67197697N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methyl-methanesulfonamideAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

1.58 g (6.96 mmol) of N-(3-acetyl-phenyl)-N-methyl-methanesulfonamide were dissolved in 15 ml of N,N-dimethylformamide dimethylacetal and the resultant solution was refluxed for 18 hours. The excess of volatile reagent was removed by reduced pressure distillation to yield a crude which was chromatographied over silica gel using a gradient of ethyl acetate/methanol as eluent. 1.12 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methyl methanesulfonamide as a yellowish-white solid were obtained (yield 88.6%).

Aufarbeitung

  1. customThe excess of volatile reagent was removed by reduced pressure distillation
  2. customto yield a crude which

Quellen und Nachweise

ORD-Eintrag
ord-d716f83265e948189c7995b734f245f3
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947688B2

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