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

HRID 745193

Reaktionsgleichung

Reaktionsgleichung von HRID 745193
[C:1]1([S:7]([CH2:10][CH2:11][NH2:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14].[CH2:25]([N:27]([CH2:34][CH3:35])[CH2:28][CH2:29][NH:30][CH:31]([CH3:33])[CH3:32])[CH3:26]>O1CCCC1>[CH2:34]([N:27]([CH2:25][CH3:26])[CH2:28][CH2:29][N:30]([CH:31]([CH3:33])[CH3:32])[C:13]([NH:12][CH2:11][CH2:10][S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])=[O:14])[CH3:35]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 35454972-(Benzenesulfonyl)ethan-1-amineHCID 12639037Diethyl((2-((propan-2-yl)amino)ethyl))amine

Produkt 1

HCID 20152862N-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N'-[2-(phenylsulfonyl)ethyl]urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 6.96 g (0.0376 mole) of 2-phenylsulfonylethanamine and 6.64 g (0.041 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 6.16 g (0.039 mole) of N-[2-(diethylamino)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the mixture was refluxed for 13 hr. The solvent was removed in vacuo, and the residue was dissolved in a 50/50 mixture of ether and methylene chloride. The solution was extracted with water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. Flash chromatography on silica gel (methanol) gave 5.74 g (41.36%) of clear, colorless oil: 1H NMR (CDCl3)δ8.5 (br s, 1, NH) 7.46-8.05 (m, 5, aromatic), 4.45 (m, 1, (CH3)2CH), 3.48 (br s, 4, SO2CH2CH 2), 3.0 (t, 2, (CH2CH2N-Et2) 2.3-2.8 (m, 6, CH2N CH2N(CH2CH3)2), 0.90-1.2 (m, 12, CH3 groups).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 13 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in a 50/50 mixture of ether and methylene chloride
  4. extractionThe 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. customFlash chromatography on silica gel (methanol) gave 5.74 g (41.36%) of clear, colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-0a0c049c547b4c5a88247500ca4f1e1e
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04597902

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