Reaktion #4310

Reaktionsgleichung

acetone ethyl acetate

1,1'-carbonyldiimidazole

N-methyl-N-(2-phenylethyl)-1,2-ethanediamine

1-methyl-N-[2-(phenylsulfonyl)ethyl]ethanamine

→

N-(1-Methylethyl)-N'-[2-[methyl-(2-phenylethyl)amino]ethyl]-N-[2-(phenylsulfonyl)ethyl]urea hemihydrate

Lösungsmittel

ether

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was heated
2. 2
   Temperaturat gentle reflux overnight
3. 3
   Extraktionextracted with water
4. 4
   ExtraktionThe organic phase was extracted with 1N sulfuric acid
5. 5
   Extraktion(Approximately half the product was extracted with acid and half
6. 6
   ExtraktionThe oganic layer was extracted with dilute sodium hydroxide
7. 7
   Sonstigedried
8. 8
   Filtrationfiltered
9. 9
   Sonstigethe solvent removed
10. 10
    Sonstigeto give an oil

Vorschrift

A solution of 1,1'-carbonyldiimidazole (8.12 g, 0.05 mole) and N-methyl-N-(2-phenylethyl)-1,2-ethanediamine, 8.0 g (0.0045 mole) in 300 ml of tetrahydrofuran was stirred for 2 hours at room temperature. To the mixture was added 9.37 g (0.0412 mole) of 1-methyl-N-[2-(phenylsulfonyl)ethyl]ethanamine and the reaction was heated at gentle reflux overnight. The reaction was stripped to dryness and dissolved in chloroformdiethyl ether (50-50 v/v) and extracted with water. The organic phase was extracted with 1N sulfuric acid. (Approximately half the product was extracted with acid and half remained in the organic layer). The oganic layer was extracted with dilute sodium hydroxide, dried, filtered, and the solvent removed to give an oil. The oil was subjected to column chromatography on Silica Gel using acetone-ethyl acetate as a eluant. This furnished 0.5 g (2.8%) of oil.

Quelle