Reacción #4310

Ecuación de reacción

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

Disolventes

ether

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction was heated
2. 2
   Temperaturaat gentle reflux overnight
3. 3
   Extracciónextracted with water
4. 4
   ExtracciónThe organic phase was extracted with 1N sulfuric acid
5. 5
   Extracción(Approximately half the product was extracted with acid and half
6. 6
   ExtracciónThe oganic layer was extracted with dilute sodium hydroxide
7. 7
   Otrodried
8. 8
   Filtraciónfiltered
9. 9
   Otrothe solvent removed
10. 10
    Otroto give an oil

Procedimiento

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.

Fuente