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

HRID 745189

Reaktionsgleichung

Reaktionsgleichung von HRID 745189
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([N:15]([CH2:20][CH3:21])[CH2:16][CH:17]([NH2:19])[CH3:18])[CH3:14].[C:22]1([S:28]([CH2:31][CH2:32][NH:33][CH:34]([CH3:36])[CH3:35])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[CH2:13]([N:15]([CH2:20][CH3:21])[CH2:16][CH:17]([NH:19][C:1](=[O:2])[N:33]([CH:34]([CH3:36])[CH3:35])[CH2:32][CH2:31][S:28]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)(=[O:29])=[O:30])[CH3:18])[CH3:14]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 13655034N-(2-phenylsulfonylethyl)-2-propanamineHCID 16643481(2-Aminopropyl)diethylamine

Produkt 1

HCID 20152789N'-[2-(Diethylamino)-1-methylethyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]ureaAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 12.15 g (0.075 mole) of 1,1'-carbonyl diimidazole and 7.50 g (0.0476 mole) of 1-diethylamino-2-propanamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 12.26 g (0.054 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the solution was refluxed for 19 hr. The solvent was removed in vacuo, and the residue was dissolved in a 50/50 mixture of methylene chloride and ether. The organic solution was extracted with several portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. Flash chromatography on silica gel (elution with methanol) gave 10.87 g (52.3 g) of clear colorless oil. 1H NMR (CDCl3)δ7.5-8.15 (m, s. aromatic), 5.35 (br s, 1, NH), 4.1 (m, 1, (CH3)2CH), 3.45-4.0 (m, 1. NHCH(CH3)CH2), 2.5-2.85 (m, 6, CH2CH3)), 0.85-1.3 (m, 15, CH3 groups).

Aufarbeitung

  1. temperaturethe solution was refluxed for 19 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in a 50/50 mixture of methylene chloride and ether
  4. extractionThe organic solution was extracted with several 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-d6f7b9cd8a144e3088b7dc53097cca2d
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04597902

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