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

HRID 330395

Reaktionsgleichung

Reaktionsgleichung von HRID 330395
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]

Komponenten

8

Edukt 4

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

Produkt 1

HCID 70360583N,N-Diethyl-N'-[2-(phenylthio)ethyl]-1,2-ethanediamine maleateAusbeute 43,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-bcff8b349aab40b9b5a7f15dcfc6c44d
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04895840

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