N,N-Diethylethylenediamine → N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[2-(phenylsulfinyl)ethyl]urea

HRID 745191

Reaktionsgleichung

Reaktionsgleichung von HRID 745191
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH2:18])[CH3:14].[C:21]1([S:27]([CH2:29][CH2:30][NH:31][CH:32]([CH3:34])[CH3:33])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH:18][C:1](=[O:2])[N:31]([CH:32]([CH3:34])[CH3:33])[CH2:30][CH2:29][S:27]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:28])[CH3:14]

Komponenten

5

Edukt 3

HCID 60993N,N-DiethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 13655080N-[2-(phenylsulfinyl)ethyl]-2-propanamine

Produkt 1

HCID 20152795N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[2-(phenylsulfinyl)ethyl]ureaAusbeute 55,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 4.70 g (0.029 mole) of 1,1'-carbonyldiimidazole- and 3.07 g (0.0265 mole) of N,N-diethylethylenediamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 8.00 g (0.0245 mole) of N-[2-(phenylsulfinyl)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the mixture was refluxed for 16 hr. The solvent was removed in vacuo, and the residue was dissolved in ether. The ether solution was extracted with several portions of water. The aqueous extract was extracted with ether and then with methylene chloride; these organic extracts were combined with the original ether solution. The organic solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil. Flash chromatography on silica gel (methanol) gave 4.84 g (55.9%) of oil: 1H NMR (CDC3), δ7.4-7.75 (m, 5, aromatic), 5.5) (br s, 1, NH) 4.12 (m, 1, (CH3)2CH), 2.8-3.7 (m, 6, SOCH2CH2 and NHCH2), 2.3-2.75 (m, 6, CH2N(CH2CH3)2), 0.8-1.3 (m, 12, CH3 groups).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 16 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ether
  4. extractionThe ether solution was extracted with several portions of water
  5. extractionThe aqueous extract
  6. extractionwas extracted with ether
  7. dry with materialThe organic solution was dried over magnesium sulfate
  8. customthe solvent was removed in vacuo
  9. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-5438944b585246fd8fcd22c762032d19
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04597902

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