1,1'-Carbonyldiimidazole → N'-[4-(Diethylamino)butyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea

HRID 4220

Reaktionsgleichung

Reaktionsgleichung von HRID 4220
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([N:15]([CH2:21][CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH3:14].[C:23]1([S:29]([CH2:32][CH2:33][NH:34][CH:35]([CH3:37])[CH3:36])(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[CH2:13]([N:15]([CH2:21][CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:1](=[O:2])[N:34]([CH:35]([CH3:37])[CH3:36])[CH2:33][CH2:32][S:29]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:30])=[O:31])[CH3:14]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 117976N,N-Diethyl-1,4-butanediamineHCID 13655034N-(2-phenylsulfonylethyl)-2-propanamine

Produkt 1

HCID 20152821N'-[4-(Diethylamino)butyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]ureaAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 4.40 g (0.0272 mole) of 1,1'-carbonyldiimidazole and 3.46 g (0.024 mole) of N,N-diethyl-1,4-butanediamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 5.00 g (0.0220 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the solution was refluxed overnight. The solvent was removed in vacuo, and the residue was dissolved in 600 ml of a 50/50 mixture of ether and methylene chloride. The organic solution was extracted with three portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. Flash chromatography on silica gel (methanol) gave 2.29 g (26.2%) of clear colorless oil:

Aufarbeitung

  1. temperaturethe solution was refluxed overnight
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 600 ml of a 50/50 mixture of ether and methylene chloride
  4. extractionThe organic solution was extracted with three portions of water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-ef1535005443433a943b7d450a9fc636
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04724235

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