Water → 1-(6-Ethoxy-carbonylhexyl)-2,4,5-triphenylimidazole

HRID 265358

Reaktionsgleichung

Reaktionsgleichung von HRID 265358
[C:1]1([C:7]2[NH:8][C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].BrC[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=O.O.CN(C)[CH:41]=[O:42]>>[CH2:36]([O:35][C:33](=[C:41]=[O:42])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][N:11]1[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:9]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:8]=[C:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:37]

Komponenten

6

Edukt 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 102322,4,5-TriphenylimidazoleHCID 24758Sodium hydrideHCID 122490Ethyl 7-bromoheptanoate

Produkt 1

HCID 867510781-(6-Ethoxy-carbonylhexyl)-2,4,5-triphenylimidazoleAusbeute 41 %

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

2,4,5-Triphenylimidazole (1.3 g) was added to a suspension of sodium hydride (0.23 g) (50% dispersion in oil, washed with hexane) in dry dimethylformamide (40 ml) under nitrogen. The reaction was stirred at 45° C. for 1.5 h, cooled and ethyl 7-bromoheptanoate (1.1 g) in dry dimethylformamide (10 ml) was added. The reaction was stirred at 50° C. for 5 h, cooled and water was carefully added. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (100 ml). The organic solution was washed with saturated sodium chloride solution (150 ml), water (100 ml), dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo. The residue was chromatographed on silica gel eluted with a dichloro-methane:ethanol gradient to give 1-(6-ethoxy-carbonylhexyl)-2,4,5-triphenylimidazole (0.81 g, 41%) as an oil. Found: C, 79.74; H, 7.32; N, 6.12%; C30H32N2O2 requires: C, 79.61; H, 7.13; N, 6.19%.

Aufarbeitung

  1. temperaturecooled
  2. stirringThe reaction was stirred at 50° C. for 5 h
  3. temperaturecooled
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  6. washThe organic solution was washed with saturated sodium chloride solution (150 ml), water (100 ml)
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated to dryness in vacuo
  9. customThe residue was chromatographed on silica gel
  10. washeluted with a dichloro-methane

Quellen und Nachweise

ORD-Eintrag
ord-023f70a95cd24f09809a91d2f82fcf73
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648373

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