Methanol → 1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-1H-indole-3-sulfonic Acid

HRID 23418

Reaktionsgleichung

Reaktionsgleichung von HRID 23418
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.C[Si]([O:20][S:21](Cl)(=[O:23])=[O:22])(C)C.CO>ClC(Cl)C>[NH:3]1[CH2:4][CH2:5][N:1]=[C:2]1[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([S:21]([OH:23])(=[O:22])=[O:20])=[CH:8]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 78059Trimethylsilyl chlorosulphateHCID 225740011-(4,5-Dihydro-1H-imidazol-2-ylmethyl)-1H-indole

Produkt 1

HCID 225740321-(4,5-dihydro-1H-imidazol-2-ylmethyl)-1H-indole-3-sulfonic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

1-(4,5-Dihydro-1H-imidazol-2-ylmethyl)-1H-indole (1.0 g, 4.243 mmol) was dissolved/suspended in dichloroethane (120 ml) and cooled in ice under a nitrogen atmosphere. Trimethylsilylchlorosulfonate (0.654 ml, 0.801 g, 4.243 mmol) was added to the cooled solution dropwise with stirring. The mixture was allowed to warm up to room temperature with stirring, and stirring was continued overnight. Methanol (20 mL) was then added, followed by stirring at room temperature for 20 minutes. The mixture was then rotovapped to dryness. The crude product was recrystallized from MeOH/EtOAc as the hydrochloride salt of 1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-1H-indole-3-sulfonic acid.

Aufarbeitung

  1. temperaturecooled in ice under a nitrogen atmosphere
  2. stirringwith stirring
  3. stirringstirring
  4. stirringby stirring at room temperature for 20 minutes
  5. customThe crude product was recrystallized from MeOH/EtOAc as the hydrochloride salt of 1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-1H-indole-3-sulfonic acid

Quellen und Nachweise

ORD-Eintrag
ord-d6b16d7c07814c4788a5b54d5ffb8990
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852726B2

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