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Imidazole → 1-[2-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethyl]-1H-imidazole

HRID 420198
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 420198
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]([CH2:20][CH2:21]OS(C)(=O)=O)[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:27]1[CH:31]=[CH:30][N:29]=[CH:28]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.C(#N)C>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]([CH2:20][CH2:21][N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 59021717Methanesulfonic acid 2-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethyl ester

Produkt 1

HCID 117175921-[2-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethyl]-1H-imidazoleAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Methanesulfonic acid 2-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethyl ester (0.250 g, 9.634 mmol), imidazole (0.173 g, 2.54 mmol), potassium carbonate (0.175 g, 1.27 mmol) and potassium iodide (0.25 g) were added to 50 mL of acetonitrile, and the reaction mixture was refluxed for 16 hours under argon. The reaction mixture was cooled and poured into 300 mL of water, extracted twice with 250 mL of EtOAc, and the combined organic layers were washed with water, saturated brine, and dried (MgSO4). The solvent was removed under reduced pressure to yield an oil that was purified via silica gel column, eluting with MeOH/CHCl3 (5:95). Solvent was removed under reduced pressure to afford 0.180 g (0.491 mmol, 77.5% of 1-[2-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-ethyl]-1H-imidazole as an oil. The oil was recrystallized from EtOH/HCl to give 0.130 g of the corresponding hydrochloride salt (0.323 mol, 50.9%). MS: 367 (M+H)+.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 16 hours under argon
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted twice with 250 mL of EtOAc
  4. washthe combined organic layers were washed with water, saturated brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed under reduced pressure
  7. customto yield an oil that
  8. customwas purified via silica gel column
  9. washeluting with MeOH/CHCl3 (5:95)
  10. customSolvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2988beafbcb64ad99dbb562a561f9064
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08093424B2

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