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N,N-Diethylethylenediamine → N'-[2-(Diethylamino)ethyl]-N-[2-[(4-methoxyphenyl)sulfonyl]ethyl]-N-(1-methylethyl)urea

HRID 4217
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 4217
[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].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH2:32][CH2:33][NH:34][CH:35]([CH3:37])[CH3:36])(=[O:31])=[O:30])=[CH:25][CH:24]=1>O1CCCC1>[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH:18][C:1](=[O:2])[N:34]([CH2:33][CH2:32][S:29]([C:26]1[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:28][CH:27]=1)(=[O:30])=[O:31])[CH:35]([CH3:37])[CH3:36])[CH3:14]
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Komponenten

5

Edukt 3

HCID 60993N,N-DiethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 13655063N-[2-[(4-methoxyphenyl)sulfonyl]ethyl]-2-propanamine

Produkt 1

HCID 13655132N'-[2-(Diethylamino)ethyl]-N-[2-[(4-methoxyphenyl)sulfonyl]ethyl]-N-(1-methylethyl)ureaAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

A solution of 4.54 g (0.28 mole) of 1,1'-carbonyldiimidazole and 2.90 g (0.025 mole) of N,N-diethylethylenediamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 5.89 g (0.0229 mole) of N-[2-[(4-methoxyphenyl)sulfonyl]ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the mixture was refluxed overnight. The solvent was removed in vacuo, and the residue was dissolved in 800 ml of a 50/50 mixture of methylene chloride-ether. The organic solution was extracted with water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. This was crystallized from ether-hexane to give 6.16 g (67.3%) of white crystalline solid; m.p. 39.5°-42° C.

Aufarbeitung

  1. temperaturethe mixture was refluxed overnight
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 800 ml of a 50/50 mixture of methylene chloride-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. customto give an oil
  8. customThis was crystallized from ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-d4c4a71d951f42169d6ac22f3b988c3e
Quelldatensatz
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04724235

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