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

HRID 330395

反応式

HRID 330395 の反応式
Cl[CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][NH2:16])[CH3:12].C(=O)([O-])[O-].[Na+].[Na+].[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]\[C:28]([OH:30])=[O:29]>C(#N)C.CO.C(OCC)C>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]\[C:28]([OH:30])=[O:29].[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][NH:16][CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:12]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 21702((2-Chloroethyl)thio)benzeneHCID 60993N,N-DiethylethylenediamineHCID 444266Maleic Acid

生成物 1

HCID 70360583N,N-Diethyl-N'-[2-(phenylthio)ethyl]-1,2-ethanediamine maleate収率 43.2%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

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.

後処理

  1. temperaturewas refluxed for 16 hr
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  4. dry with materialThe methylene chloride solution was dried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give an oil
  7. customA white solid precipitated at -5° C.

出典と根拠

ORDレコード
ord-bcff8b349aab40b9b5a7f15dcfc6c44d
出典データセット
uspto-grants-1990_01
特許番号
US04895840

関連ノート

読み込み中…