Reaktion #4311

Reaktionsgleichung

Florisil

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

1,1'-carbonyldiimidazole

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

→

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

Lösungsmittel

tetrahydrofuran

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting solution heated overnight at gentle reflux
2. 2
   Sonstigepartitioned between chloroform and water
3. 3
   Sonstigeremoval of chloroform
4. 4
   Sonstigegave a dark brown oil
5. 5
   Extraktionextracted with 1N sulfuric acid (saturated with sodium chloride)
6. 6
   Extraktionextracted with chloroform
7. 7
   Sonstigethe solvent removed
8. 8
   Sonstigeto give a light brown oil
9. 9
   Wascheneluted with methanol-methylene chloride
10. 10
    Sonstigeremoving solvent
11. 11
    Sonstigean oil was obtained
12. 12
    SonstigeThe oil was triturated with diethyl ether
13. 13
    Sonstigedried at 80° C. in vacuo overnight

Vorschrift

A solution of 17.90 g (0.045 mole) of N-methyl-N-(phenylmethyl)-1,2-ethanediamine and 1,1'-carbonyldiimidazole (0.05 mole) in 100 ml of tetrahydrofuran was stirred at room temperature for 1 hour. To the mixture was added 10.52 g, (0.04 mole) of 1-methyl-N-[2-(phenysulfonyl)ethyl]ethanamine and the resulting solution heated overnight at gentle reflux. The reaction mixture was stripped to dryness and partitioned between chloroform and water; removal of chloroform gave a dark brown oil. The oil was dissolved in chloroform and extracted with 1N sulfuric acid (saturated with sodium chloride). The acidic layer was made alkaline, extracted with chloroform, and the solvent removed to give a light brown oil. The oil was subjected to chromatography on a Florisil column and eluted with methanol-methylene chloride. After combining appropriate fractions from the column and removing solvent, an oil was obtained. The oil was triturated with diethyl ether and dried at 80° C. in vacuo overnight. This furnished 6.75 g (40.4%) of clear oil.

Quelle