Réaction #4311

Équation de réaction

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

Solvants

tetrahydrofuran

chloroform

Conditions de réaction

Traitement

1. 1
   Températurethe resulting solution heated overnight at gentle reflux
2. 2
   Autrepartitioned between chloroform and water
3. 3
   Autreremoval of chloroform
4. 4
   Autregave a dark brown oil
5. 5
   Extractionextracted with 1N sulfuric acid (saturated with sodium chloride)
6. 6
   Extractionextracted with chloroform
7. 7
   Autrethe solvent removed
8. 8
   Autreto give a light brown oil
9. 9
   Lavageeluted with methanol-methylene chloride
10. 10
    Autreremoving solvent
11. 11
    Autrean oil was obtained
12. 12
    AutreThe oil was triturated with diethyl ether
13. 13
    Autredried at 80° C. in vacuo overnight

Mode opératoire

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.

Source