反応 #417577

反応方程式

maleic acid

[(2-chloroethyl)thio]benzene

N,N-diethylethylenediamine

sodium carbonate

→

title compound

収率 43.2%

N,N-Diethyl-N'-[2-(phenylthio)ethyl]-1,2-ethanediamine maleate

収率 43.2%

溶媒

methanol

diethyl ether

methanol

acetonitrile

反応条件

後処理

1. 1
   温度was refluxed for 16 hr
2. 2
   その他The solvent was removed in vacuo
3. 3
   その他the residue was partitioned between methylene chloride and dilute sodium hydroxide
4. 4
   乾燥The methylene chloride solution was dried over sodium sulfate
5. 5
   その他the solvent was removed in vacuo
6. 6
   その他to give an oil
7. 7
   その他A white solid precipitated at -5° C.

実験手順

A mixture of 60.24 g (0.350 mole) of [(2-chloroethyl)thio]benzene, 84 g (0.72 mole) of N,N-diethylethylenediamine, and 80.0 g (0.75 mole) of sodium carbonate in 1.5 liters of acetonitrile was refluxed for 16 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over sodium sulfate, and the solvent was removed in vacuo to give an oil. This was dissolved in 800 ml of methanol. A solution of approximately 2 equivalents of maleic acid in methanol was added followed by the addition of anhydrous diethyl ether until the solution became slightly cloudy. A white solid precipitated at -5° C. to give 73.15 g (43.2%) of title compound, a white crystalline solid, mp 131°-133° C.

出典