反応 #4311

反応方程式

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

溶媒

tetrahydrofuran

chloroform

反応条件

後処理

1. 1
   温度the resulting solution heated overnight at gentle reflux
2. 2
   その他partitioned between chloroform and water
3. 3
   その他removal of chloroform
4. 4
   その他gave a dark brown oil
5. 5
   抽出extracted with 1N sulfuric acid (saturated with sodium chloride)
6. 6
   抽出extracted with chloroform
7. 7
   その他the solvent removed
8. 8
   その他to give a light brown oil
9. 9
   洗浄eluted with methanol-methylene chloride
10. 10
    その他removing solvent
11. 11
    その他an oil was obtained
12. 12
    その他The oil was triturated with diethyl ether
13. 13
    その他dried at 80° C. in vacuo overnight

実験手順

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.

出典