N,N-Diethylethylenediamine → N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]thiourea

HRID 4219

Reaktionsgleichung

Reaktionsgleichung von HRID 4219
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[C:9](N1C=CN=C1)(N1C=CN=C1)=[S:10].[C:21]1([S:27]([CH2:30][CH2:31][NH:32][CH:33]([CH3:35])[CH3:34])(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:6][C:9](=[S:10])[N:32]([CH:33]([CH3:35])[CH3:34])[CH2:31][CH2:30][S:27]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)(=[O:28])=[O:29])[CH3:2]

Komponenten

5

Edukt 3

HCID 60993N,N-DiethylethylenediamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 13655034N-(2-phenylsulfonylethyl)-2-propanamine

Produkt 1

HCID 13655153N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]thioureaAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 2.78 g (0.024 mole) of N,N-diethylethylenediamine and 4.82 g (0.027 mole) of 1,1'-thiocarbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 5.00 g (0.022 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine in 100 ml of tetrahydrofuran was added, and the solution was refluxed for 48 hrs. The solvent was removed in vacuo and the residue was dissolved in 400 ml of a 50/50 mixture of methylene chloride and ether. The organic solution was extracted with water and was dried over magnesium sulfate. The solvent was removed in vacuo, and the residue was recrystallized from a mixture of methylene chloride-ether-hexane to give 5.95 g (72.5%) of pale yellow solid, m.p.81.5°-82.5° C.

Aufarbeitung

  1. temperaturethe solution was refluxed for 48 hrs
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 400 ml of a 50/50 mixture of methylene chloride and ether
  4. extractionThe organic solution was extracted with water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was recrystallized from a mixture of methylene chloride-ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-00fb66882c6644f8a3f0fc09bf6d44fa
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04724235

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