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

HRID 330397Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 330397
Cl[CH2:2][CH2:3][S:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH2:12]([N:14]([CH2:18][CH3:19])[CH2:15][CH2:16][NH2:17])[CH3:13].C(=O)([O-])[O-].[Na+].[Na+].[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30]>C(#N)C.CO.C(OCC)C>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30].[CH2:12]([N:14]([CH2:18][CH3:19])[CH2:15][CH2:16][NH:17][CH2:2][CH2:3][S:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:13]

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 60993N,N-DiethylethylenediamineHCID 99293((2-Chloroethyl)sulphinyl)benzeneHCID 444266Maleic Acid

Produkt 1

HCID 70361008N,N-Diethyl-N'-[2-(phenylsulfinyl)ethyl]-1,2-ethanediamine maleateAusbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 20.0 g (0.106 mole) of [(2-chloroethyl)sulfinyl]benzene, 30.0 g (0.259 mole) of N,N-diethylethylenediamine and excess sodium carbonate in 600 ml of acetonitrile was refluxed for 16 hr. The reaction mixture solution was filtered, and the solvent was removed in vacuo. 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 methanol, and a solution of 2 equivalents of maleic acid in methanol was added. Diethyl ether was added and a whie solid precipitated to give 26.7 g (50.3%) of title compound, a white crystalline solid, mp 111°-112.5° C.

Aufarbeitung

  1. temperaturewas refluxed for 16 hr
  2. filtrationThe reaction mixture solution was filtered
  3. customthe solvent was removed in vacuo
  4. customThe residue was partitioned between methylene chloride and dilute sodium hydroxide
  5. dry with materialThe methylene chloride solution was dried over sodium sulfate
  6. customthe solvent was removed in vacuo
  7. customto give an oil
  8. customa whie solid precipitated

Quellen und Nachweise

ORD-Eintrag
ord-78f46fb1e0ea463099ce75c3e46f1862
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04895840

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